Skip to main content
SpringerLink
Log in

Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

Abstract

Dimethyl sulfoxide (DMSO), as extremely important aprotic polar solvent and reaction medium, has attracted widespread attention from chemists in recent years due to its wide range of uses and the multiple functions it displays in various chemical processes. Especially in the past decade, dimethyl sulfoxide has become increasingly favored as a synthon in organic chemistry, resulting in great progress in this research field. In this context, this review provides a comprehensive summary of the literature on the recent progress in organic synthesis using dimethyl sulfoxide as a synthon, covering all the reports from 1 January 2016 to 11 May 2022. This type of reaction is mainly performed by transferring one or more units of dimethyl sulfoxide, such as oxygen (–O–, =O), methyl (–CH3), methylene (–CH2–), methylidene (=CH2), methine (=CH–), donor of formylation (–CHO), sulfur (–S–), methylthio (–SMe), methyl sulfoxide (–SOMe), donor of methyl thiomethylation (–CH2SMe), or donor of methyl sulfoxide methylation (–CH2SOMe), to the target molecules. At the same time, we hope that this review will stimulate future studies and promote developments in this area.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32
Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Scheme 39
Scheme 40
Scheme 41
Scheme 42
Scheme 43
Scheme 44
Scheme 45
Scheme 46
Scheme 47
Scheme 48
Scheme 49
Scheme 50
Scheme 51
Scheme 52
Scheme 53
Scheme 54
Scheme 55
Scheme 56
Scheme 57
Scheme 58
Scheme 59
Scheme 60
Scheme 61
Scheme 62
Scheme 63
Scheme 64
Scheme 65
Scheme 66
Scheme 67
Scheme 68
Scheme 69
Scheme 70
Scheme 71
Scheme 72
Scheme 73
Scheme 74
Scheme 75
Scheme 76
Scheme 77
Scheme 78
Scheme 79
Scheme 80
Scheme 81
Scheme 82
Scheme 83
Scheme 84
Scheme 85
Scheme 86
Scheme 87
Scheme 88
Scheme 89
Scheme 90
Scheme 91
Scheme 92
Scheme 93
Scheme 94
Scheme 95
Scheme 96
Scheme 97
Scheme 98
Scheme 99
Scheme 100
Scheme 101
Scheme 102
Scheme 103
Scheme 104
Scheme 105
Scheme 106
Scheme 107
Scheme 108
Scheme 109
Scheme 110
Scheme 111

Similar content being viewed by others

Abbreviations

DMSO:

Dimethyl sulfoxide

DMS:

Dimethyl sulfide

CuI:

Cuprous iodide

CuBr2 :

Copper(II) bromide

TEMPO:

2,2,6,6-Tetramethylpiperidine-1-oxyl

AgTFA:

Silver trifluoroacetate

(COCl)2 :

Carbonyl chloride

CH3CN:

Acetonitrile

CHCl3 :

Trichloromethane

CH2Cl2 :

Dichloromethane

FeCl2 :

Ferrous chloride

H2O2 :

Hydrogen peroxide

TMSN3 :

Trimethylsilyl azide

FeSO4 :

Ferrous sulfate

K2S2O8 :

Potassium persulfate

DABCO:

1,4-Diazabicyclo[2.2.2]octane

tBuONa:

Sodium tert-butoxide

TDMSOI:

Trideuteromethyl sulfoxonium iodide

TMSOI:

Trimethyl sulfoxonium iodide

DMSO-d 6 :

(Methyl sulfoxide)-d6

tBuOK:

Potassium tert-butoxide

H3PO4 :

Phosphoric acid

DMPU:

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

Tf2O:

Trifluoromethanesulfonic anhydride

AcCl:

Acetyl chloride

Pd(OAc)2 :

Palladium acetate

KHSO5 :

Potassium monopersulfate triple salt

Pd(dba)2 :

Bis(dibenzylideneacetone)palladium

DABSO:

Bis(sulfur dioxide)-1,4-diazabicyclo[2.2.2]octane adduct

THIQ:

1,2,3,4-Tetrahydroisoquinoline

TMEDA:

Trimethylethylenediamine

TsOH:

4-Methylbenzenesulfonic acid

TFA:

Trifluoroacetic acid

TBHP:

tert-Butyl hydroperoxide

Zn(OTf)2 :

Zinc trifluoromethanesulfonate

BHT:

Butylated hydroxytoluene

PhI(OAc)2 :

(Diacetoxyiodo)benzene

NH4OAc:

Ammonium acetate

NBS:

N-Bromosuccinimide

References

  1. Brayton CF (1986) Dimethyl sulfoxide (DMSO): a review. Cornell Vet 76:61–90

    PubMed  CAS  Google Scholar 

  2. Santos NC, Figueira-Coelho J, Martins-Silva J, Saldanha C (2003) Multidisciplinary utilization of dimethyl sulfoxide: pharmacological, cellular, and molecular aspects. Biochem Pharmacol 65:1035–1041

    Article  PubMed  CAS  Google Scholar 

  3. Yang X-W, Zhang X-Y, Guo Z-C, Bai W-S, Hao L, Wei H-Y (2013) Effects of incompatible substances on the thermal stability of dimethyl sulfoxide. Thermochim Acta 559:76–81

    Article  CAS  Google Scholar 

  4. Cardillo P, Girelli A (1982) Thermal stability of dimethyl sulfoxide under adiabatic conditions. Chim Ind 64:231–234

    CAS  Google Scholar 

  5. Clark T, Murray JS, Lane P, Politzer P (2008) Why are dimethyl sulfoxide and dimethyl sulfone such good solvents? J Mol Model 14:689–697

    Article  PubMed  CAS  Google Scholar 

  6. Galvao J, Davis B, Tilley M, Normando E, Duchen MR, Cordeiro MF (2014) Unexpected low-dose toxicity of the universal solvent DMSO. FASEB J 28:1317–1330

    Article  PubMed  CAS  Google Scholar 

  7. Wen Y-C, Kuo H-C, Guo J-L, Jia H-W (2016) Nuclear magnetic resonance spectroscopy investigation on ultralow melting temperature behavior of dimethyl sulfoxide-water solutions. J Phys Chem B 120:13125–13135

    Article  PubMed  CAS  Google Scholar 

  8. Kiefer J, Noack K, Kirchner B (2011) Hydrogen bonding in mixtures of dimethyl sulfoxide and cosolvents. Curr Phys Chem 1:340–351

    Article  CAS  Google Scholar 

  9. McKim AS, Strub R (2008) Dimethyl sulfoxide USP, PhEur in approved pharmaceutical products and medical devices. Pharm Technol 32:74–85

    CAS  Google Scholar 

  10. Soroko I, Bhole Y, Livingston AG (2011) Environmentally friendly route for the preparation of solvent resistant polyimide nanofiltration membranes. Green Chem 13:162–168

    Article  CAS  Google Scholar 

  11. Coly A, Aaron JJ (1994) Photochemical-spectrofluorimetric method for the determination of several aromatic insecticides. Analyst 119:1205–1209

    Article  CAS  Google Scholar 

  12. Montesinos T, Perez-Munguia S, Valdez F, Marty J-L (2001) Disposable cholinesterase biosensor for the detection of pesticides in water-miscible organic solvents. Anal Chim Acta 431:231–237

    Article  CAS  Google Scholar 

  13. Mohanty E, Singh BC (1998) Graft Copolymerization of methyl methacrylate onto jute fiber initiated by cerium(IV)​-​DMSO redox initiator system. J Appl Polym Sci 69:2569–2576

    Article  CAS  Google Scholar 

  14. Deguchi Y, Kono M, Koizumi Y, Watanabe Y, Fujita M, Izato Y-I, Miyake A (2021) Study on autocatalytic decomposition of dimethyl sulfoxide (DMSO) II: analysis of intermediate substances obtained in the induction period and investigations regarding formic acid. Org Process Res Dev 25:2658–2668

    Article  CAS  Google Scholar 

  15. Gao F, Bai RX, Ferlin F, Vaccaro L, Li MH, Gu YL (2020) Replacement strategies for non-​green dipolar aprotic solvents. Green Chem 22:6240–6257

    Article  CAS  Google Scholar 

  16. Barnes JD, Balaguer L, Manrique E, Elvira S, Davison AW (1992) A reappraisal of the use of DMSO for the extraction and determination of chlorophylls A and B in lichens and higher plants. Environ Exp Bot 32:85–100

    Article  CAS  Google Scholar 

  17. Kumar B, Jain SK, Prajapati SK (2011) Effect of penetration enhancer DMSO on in-​vitro skin permeation of acyclovir transdermal microemulsion formulation. Int J Drug Deliv 3:83–94

    Article  CAS  Google Scholar 

  18. Mok H, Park TG (2008) Direct plasmid DNA encapsulation within plga nanospheres by single oil-​in-​water emulsion method. Eur J Pharm Biopharm 68:105–111

    Article  PubMed  CAS  Google Scholar 

  19. Wath SB, Katariya MN, Singh SK, Kanade GS, Vaidya AN (2015) Separation of WPCBs by dissolution of brominated epoxy resins using DMSO and NMP: a comparative study. Chem Eng J 280:391–398

    Article  CAS  Google Scholar 

  20. Juestel PM, Pignot CD, Ofial AR (2021) Nucleophilic reactivities of thiophenolates. J Org Chem 86:5965–5972

    Article  CAS  Google Scholar 

  21. Campos RB, Santos EH, Oliveira ARM, Ocampos FMM, Souza BS, Barison A, Orth ES (2015) Reactivity of imidazole derivatives toward phosphate triester in DMSO/water mixtures: a comprehensive study on the solvent effect. J Org Chem 80:7572–7580

    Article  PubMed  CAS  Google Scholar 

  22. Acevedo O, Jorgensen WL (2006) Cope elimination: elucidation of solvent effects from QM​/MM simulations. J Am Chem Soc 128:6141–6146

    Article  PubMed  CAS  Google Scholar 

  23. Li W, Li JC, Lin M, Wacharasindhu S, Tabei K, Mansour TS (2007) Dimethyl sulfoxide mediated elimination reactions in 3-​aryl 2,​3-​dihalopropanoates: scope and mechanistic insights. J Org Chem 72:6016–6021

    Article  PubMed  CAS  Google Scholar 

  24. Cho BR, Jang WJ, Je JT, Bartsch RA (1993) Elimination reactions of (E)​-​O-​pivaloylbenzaldoximes. J Org Chem 58:3901–3904

    Article  CAS  Google Scholar 

  25. Das E, Basak S, Anoop A, Chand S, Basak A (2019) How to achieve high regioselectivity in barrier-​less nucleophilic addition to p-​benzynes generated via bergman cyclization of unsymmetrical cyclic azaenediyne? J Org Chem 84:2911–2921

    Article  PubMed  CAS  Google Scholar 

  26. Eitzinger A, Mayer RJ, Hampel N, Mayer P, Waser M, Ofial AR (2020) Electrophilic reactivities of vinyl p-​quinone methides. Org Lett 22:2182–2186

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  27. Wu X-F, Natte K (2016) The applications of dimethyl sulfoxide as reagent in organic synthesis. Adv Synth Catal 358:336–352

    Article  CAS  Google Scholar 

  28. Jones-Mensah E, Karki M, Magolan J (2016) Dimethyl sulfoxide as a synthon in organic chemistry. Synthesis 48:1421–1436

    Article  CAS  Google Scholar 

  29. Monga A, Bagchi S, Sharma A (2018) Iodine/DMSO oxidations: a contemporary paradigm in C–N bond chemistry. New J Chem 42:1551–1576

    Article  CAS  Google Scholar 

  30. Tashrifi Z, Khanaposhtani MM, Larijanic B, Mahdavi M (2020) DMSO: yesterday’s solvent, today’s reagent. Adv Synth Catal 362:65–86

    Article  CAS  Google Scholar 

  31. Liang Y-F, Li XY, Wang XY, Zou MC, Tang CH, Liang YJ, Song S, Jiao N (2016) Conversion of simple cyclohexanones into catechols. J Am Chem Soc 138:12271–12277

    Article  PubMed  CAS  Google Scholar 

  32. Sun K, Zhu ZH, Sun JJ, Liu LL, Wang X (2016) Copper-catalyzed N-arylation of azoles and Mannich-type coupling of ketones and azoles under metal-free conditions. J Org Chem 81:1476–1483

    Article  PubMed  CAS  Google Scholar 

  33. Chan C-K, Tsai Y-L, Chang M-Y (2017) CuI mediated one-pot cycloacetalization/ketalization of o-carbonyl allylbenzenes: synthesis of benzobicyclo[3.2.1]octane core. Org Lett 19:1870–1873

    Article  PubMed  CAS  Google Scholar 

  34. Tlahuext-Aca A, Garza-Sanchez RA, Schäfer M, Glorius F (2018) Visible-light-mediated synthesis of ketones by the oxidative alkylation of styrenes. Org Lett 20:1546–1549

    Article  PubMed  CAS  Google Scholar 

  35. Ni Y, Zuo HH, Yu HB, Wu YZ, Zhong FR (2018) Synergistic catalysis-enabled thia-aza-prins cyclization with DMSO and disulfides: entry to sulfenylated 1,3-oxazinanes and oxazolidines. Org Lett 20:5899–5904

    Article  PubMed  CAS  Google Scholar 

  36. Li LX, Luo HT, Zhao ZG, Li Y, Zhou QJ, Xu J, Li J, Ma Y-N (2019) Photoredox-catalyzed remote difunctionalizations of alkenes to synthesize fluoroalkyl ketones with dimethyl sulfoxide as the oxidant. Org Lett 21:9228–9231

    Article  PubMed  CAS  Google Scholar 

  37. Fang X-X, Wang P-F, Yi W, Chen W, Lou S-C, Liu G-Q (2019) Visible-light-mediated oxidative coupling of vinylarenes with bromocarboxylates leading to γ-ketoesters. J Org Chem 84:15677–15684

    Article  PubMed  CAS  Google Scholar 

  38. Cao ZZ, Lv HF, Liu YF, Nie ZW, Liu HP, Yang TL, Luo WP, Liu Q, Guo CC (2019) Dimethyl sulfoxide oxygen donor-based annulation of ketones and ammonium persulfate: regioselective synthesis of 2,4-disubstituted oxazoles. Adv Synth Catal 361:1632–1640

    Article  CAS  Google Scholar 

  39. Li LX, Ma Y-N, Tang M, Guo J, Yang Z, Yan YZ, Ma XT, Tang L (2019) Photoredox-catalyzed oxydifluoroalkylation of styrenes for access to difluorinated ketones with DMSO as an oxidant. Adv Synth Catal 361:3723–3728

    Article  CAS  Google Scholar 

  40. Shang TB, Zhang JH, Zhang Y, Zhang F, Li X-S, Zhu GG (2020) Photocatalytic remote oxyfluoroalkylation of heteroalkynes: regio-, stereo-, and site-selective access to complex fluoroalkylated (Z)-alkenes. Org Lett 22:3667–3672

    Article  PubMed  CAS  Google Scholar 

  41. Zhang Z-W, Li H-B, Li J, Wang C-C, Feng J, Yang Y-H, Liu SX (2020) Synthesis of epoxides from alkyl bromides and alcohols with in situ generation of dimethyl sulfonium ylide in DMSO oxidations. J Org Chem 85:537–547

    Article  PubMed  CAS  Google Scholar 

  42. Lu Y, Luo M-J, Hu M, Li Y, Li J-H (2020) Dimethyl sulfoxide as an oxygen atom source enabled tandem conversion of 2-alkynyl carbonyls to 1,2-dicarbonyls. Adv Synth Catal 362:1846–1850

    Article  CAS  Google Scholar 

  43. Chun JL, Zhang HL, Meng F, Guo K, Cao SJ, Fang Q, Li J, Zhu YG (2021) Visible-light photoredox-catalyzed tandem trifluoromethylation/cyclization/remote oxidation of 1,6-dienes: access to CF3-containing five-membered heterocycles. Adv Synth Catal 363:751–756

    Article  CAS  Google Scholar 

  44. Wang H, Xi ZY, Huang S, Ding R, Gao Y, Liu YG, Sun BG, Tian HY, Liang S (2021) Convenient preparation of N-acylbenzoxazines from phenols, nitriles, and DMSO initiated by a catalytic amount of (COCl)2. J Org Chem 86:4932–4943

    Article  PubMed  CAS  Google Scholar 

  45. Fu D, Dong J, Wang JY, Xu JX (2021) Direct 1,2-oxosulfenylation of acetylenic sulfones with DMSO. Asian J Org Chem 10:1756–1764

    Article  CAS  Google Scholar 

  46. Yu X-X, Zhao P, Zhou Y, Huang C, Wang L-S, Wu Y-D, Wu A-X (2021) Employing arylacetylene as a diene precursor and dienophile: synthesis of quinoline via the povarov reaction. J Org Chem 86:8381–8388

    Article  PubMed  CAS  Google Scholar 

  47. Yu X-X, Zhao P, Zhou Y, Huang C, Wang L-S, Wu Y-D, Wu A-X (2021) Iodine-promoted formal [3+2] cycloaddition of enaminone: access to 2-hydroxy-1,2-dihydro-pyrrol-3-ones with quaternary carbon center. J Org Chem 86:12141–12147

    Article  PubMed  CAS  Google Scholar 

  48. Wang R, Xie K-J, Fu Q, Wu M, Pan G-F, Lou D-W, Lian F-S (2022) Transformation of thioacids into carboxylic acids via a visible-light-promoted atomic substitution process. Org Lett 24:2020–2024

    Article  PubMed  CAS  Google Scholar 

  49. Jin J, MacMillan DWC (2015) Alcohols as alkylating agents in heteroarene C–H functionalization. Nature 525:87–90

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  50. Uemura T, Yamaguchi M, Chatani N (2016) Phenyltrimethylammonium salts as methylation reagents in the nickel-catalyzed methylation of C−H bonds. Angew Chem Int Ed 55:3162–3165

    Article  CAS  Google Scholar 

  51. Caporaso R, Manna S, Zinken S, Kochnev AR, Lukyanenko ER, Kurkind AV, Antonchick AP (2016) Radical trideuteromethylation with deuterated dimethyl sulfoxide in the synthesis of heterocycles and labelled building blocks. Chem Commun 52:12486–12489

    Article  CAS  Google Scholar 

  52. Xie ZG, Li PH, Hu Y, Xua N, Wang L (2017) Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles. Org Biomol Chem 15:4205–4211

    Article  PubMed  CAS  Google Scholar 

  53. Zhang R, Shi XQ, Yan QQ, Li ZJ, Wang Z, Yu HF, Wang XK, Qi J, Jiang ML (2017) Free-radical initiated cascade methylation or trideuteromethylation of isocyanides with dimethyl sulfoxides. RSC Adv 7:38830–38833

    Article  CAS  Google Scholar 

  54. Zhang R, Yu HF, Li ZJ, Yan QQ, Li P, Wu JL, Qi J, Jiang ML, Su LX (2018) Iron-mediated azidomethylation or azidotrideuteromethylation of active alkenes with azidotrimethylsilane and dimethylsulfoxide. Adv Synth Catal 360:1384–1388

    Article  CAS  Google Scholar 

  55. Xu N, Zhang Y, Chen W, Li PH, Wang L (2018) Photoinduced N-methylation and N-sulfonylation of azobenzenes with DMSO under mild reaction conditions. Adv Synth Catal 360:1199–1208

    Article  CAS  Google Scholar 

  56. Xu C, Jiang S-F, Wen X-H, Zhang Q, Zhou Z-W, Wu Y-D, Jia F-C, Wu A-X (2018) Dimethyl sulfoxide serves as a dual synthon: construction of 5-methyl pyrimidine derivatives via four component oxidativeannulation. Adv Synth Catal 360:2267–2271

    Article  CAS  Google Scholar 

  57. Jiang SH, Yang ZH, Guo ZY, Li YB, Chen L, Zhu ZZ, Chen XW (2019) Transition metal-free α-methylation of 1,8-naphthyridine derivatives using DMSO as methylation reagent. Org Biomol Chem 17:7416–7424

    Article  PubMed  CAS  Google Scholar 

  58. Shen ZY, Zhang SL, Geng HH, Wang JR, Zhang XY, Zhou AQ, Yao C, Chen XB, Wang W (2019) Trideuteromethylation enabled by a sulfoxonium metathesis reaction. Org Lett 21:448–452

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  59. Yang PF, Xu WY, Wang RC, Zhang M, Xie CS, Zeng XF, Wang M (2019) Potassium tert-butoxide-mediated condensation cascade reaction: transition metal-free synthesis of multisubstituted aryl indoles and benzofurans. Org Lett 21:3658–3662

    Article  PubMed  CAS  Google Scholar 

  60. Li PF, Weng YX, Xu XX, Cui XL (2016) Access to indole derivatives from diaryliodonium salts and 2-alkynylanilines. J Org Chem 81:3994–4001

    Article  PubMed  CAS  Google Scholar 

  61. Patel OPS, Anand D, Maurya RK, Yadav PP (2016) H2O2/DMSO-promoted regioselective synthesis of 3,3′-bisimidazopyridinylmethanes via intermolecular oxidative C(sp2)−H bond activation of imidazoheterocycles. J Org Chem 81:7626–7634

    Article  PubMed  CAS  Google Scholar 

  62. Liu P, Shen ZY, Yuan Y, Sun PP (2016) Synthesis of symmetrical methylene-bridged imidazoheterocycles using DMSO as methylene source under metal-free conditions. Org Biomol Chem 14:6523–6530

    Article  PubMed  CAS  Google Scholar 

  63. Shi J, Tang X-D, Wu Y-C, Fang J-F, Cao L, Chen X-Y, Wang Z-Y (2016) A radical coupling reaction of DMSO with sodium arylsulfinates in air : mild utilization of DMSO as C1 resource for the synthesis of arylsulfonyl dibromomethane. RSC Adv 6:25651–25655

    Article  CAS  Google Scholar 

  64. Zhu XM, Li WG, Luo XA, Deng GB, Liang Y, Liu JB (2018) A catalyst-free and additive-free method for the synthesis of benzothiazolethiones from o-iodoanilines, DMSO and potassium sulfide. Green Chem 20:1970–1974

    Article  CAS  Google Scholar 

  65. Ai H-J, Qi XX, Peng J-B, Ying J, Wu X-F (2018) Palladium-catalyzed cross-coupling of arylboronic acid and benzonitriles using DMSO as the methylene source. Asian J Org Chem 7:2045–2048

    Article  CAS  Google Scholar 

  66. Gao YJ, Zhou DS, Ma YM (2018) α-Csp3-H methylenation of diketones to synthesize methylene-bridged bis-1,3-dicarbonyl compounds and polysubstituted pyridines using the DMSO/selectfluor system. ChemistrySelect 3:9374–9377

    Article  CAS  Google Scholar 

  67. Yan M, Zhou DS, Gao YJ, Ma YM (2018) Metal-free synthesis of methylene-bridged bisamide via selectfluor-mediated oxidative methylenation. ChemistrySelect 3:13006–13009

    Article  CAS  Google Scholar 

  68. Zhang X, Zhou Z, Xu HY, Xu XF, Yu XY, Yi W (2019) Cobalt-catalyzed allylation of amides with styrenes using DMSO as both the solvent and the α-methylene source. Org Lett 21:7248–7253

    Article  PubMed  CAS  Google Scholar 

  69. Li H, Liu HP, Liu YF, Cao ZZ, Su MD, Fu MQ, Luo WP, Liu Q, Guo CC (2019) Efficient synthesis of 3,6-dihydro-2H-pyrans via [3+2+1] annulation based on the heteroatom-free tri-atom donor. Adv Synth Catal 361:5392–5399

    Article  CAS  Google Scholar 

  70. Hada S, Zai MSK, Roat P, Verma VP, Shah AK, Yadav DK, Kumari N (2019) Metal-free graphene oxide promoted a novel multicomponent reaction for the synthesis of 3-substituted quinazolinones using DMSO as one carbon synthon. ChemistrySelect 4:1176–1179

    Article  CAS  Google Scholar 

  71. Ebule R, Mudshinge S, Nantz MH, Mashuta MS, Hammond GB, Xu B (2019) A 5+1 protic acid assisted aza-pummerer approach for synthesis of 4-chloropiperidines from homoallylic amines. J Org Chem 84:3249–3259

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  72. Qi ZJ, Wang HC, Ren Y, Niu YN, Jiang Y, Yan RL (2020) Synthesis of 3-benzylidenetetrahydrofurans: Tf2O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO. Chem Commun 56:15627–15630

    Article  CAS  Google Scholar 

  73. Kour J, Venkateswarlu V, Verma PK, Hussain Y, Dubey G, Bharatam PV, Sahoo SC, Sawant SD (2020) Oxone-DMSO triggered methylene insertion and C(sp2)−C(sp3)-H−C(sp2) bond formation to access functional bis-heterocycles. J Org Chem 85:4951–4962

    Article  PubMed  CAS  Google Scholar 

  74. Zhang Y, Kuang JQ, Xiao XQ, Wang L, Ma YM (2021) DMSO as a dual carbon synthon and water as oxygen donor for the construction of 1,3,5-oxadiazines from amidines. Org Lett 23:3960–3964

    Article  PubMed  CAS  Google Scholar 

  75. Li H, Su MD, Nie ZW, Yang TL, Luo WP, Liu Q, Guo CC (2021) Effective [3+1+1+1] cycloaddition to six-membered carbocycle based on DMSO as dual carbon synthon. Adv Synth Catal 363:3127–3137

    Article  CAS  Google Scholar 

  76. Shi Y, Xu XF, Chen XF, Gao WC, Zhang X (2021) Synthesis of cyclopentenes and cyclohexenes via cobalt(II)-catalyzed oxidative cyclization. J Org Chem 86:15335–15344

    Article  PubMed  CAS  Google Scholar 

  77. Kalari S, Shinde AU, Rode HB (2021) Methylene-tethered arylsulfonation and benzotriazolation of aryl/heteroaryl C−H bonds with DMSO as a one-carbon surrogate. J Org Chem 86:17684–17695

    Article  PubMed  CAS  Google Scholar 

  78. Zhang L, Liu SH, Lin YL, Wang YL (2022) Hydroxymethylation of active methenyl compounds: DMSO as methylene source and H2O as oxygen source. Tetrahedron Lett 93:153663

    Article  CAS  Google Scholar 

  79. Pothikumar R, Sujatha C, Namitharan K (2017) Transition-metal-free in situ generation of terminal alkenes: synthesis of multisubstituted acrylamidines via tandem sp3 C−H olefination/sp2 C−H arylation reactions. ACS Catal 7:7783–7787

    Article  CAS  Google Scholar 

  80. Liu Y-F, Ji P-Y, Xu J-W, Hu Y-Q, Liu Q, Luo W-P, Guo C-C (2017) Transition metal-free α-Csp3-H methylenation of ketones to form C=C bond using dimethyl sulfoxide as carbon source. J Org Chem 82:7159–7164

    Article  PubMed  CAS  Google Scholar 

  81. Nie ZW, Lv HF, Li H, Su MD, Yang TL, Luo WP, Liu Q, Guo CC (2021) Synthesis of terminal N-vinylazoles from aromatic aldehydes, DMSO, and azoles based DMSO as terminal carbon synthon. Adv Synth Catal 363:4621–4626

    Article  CAS  Google Scholar 

  82. Chakraborty N, Dahiya A, Rakshit A, Modi A, Patel BK (2021) An expedient route to tricyanovinylindoles and indolylmaleimides from o-alkynylanilines utilizing DMSO as a one-carbon synthon. Org Biomol Chem 19:6847–6857

    Article  PubMed  CAS  Google Scholar 

  83. Duan TT, Zhai TR, Liu HH, Yan ZL, Zhao Y, Feng L, Ma C (2016) One-pot three-component synthesis of quinazolines via a copper-catalysed oxidative amination reaction. Org Biomol Chem 14:6561–6567

    Article  PubMed  CAS  Google Scholar 

  84. Wu X, Zhang JJ, Liu S, Gao QH, Wu AX (2016) An efficient synthesis of polysubstituted pyridines via Csp3-H oxidation and C-S cleavage of dimethyl sulfoxide. Adv Synth Catal 358:218–225

    Article  CAS  Google Scholar 

  85. Wakade SB, Tiwari DK, Ganesh PSKP, Phanindrudu M, Likhar PR, Tiwari DK (2017) Transition-metal-free quinoline synthesis from acetophenones and anthranils via sequential one-carbon homologation/conjugate addition/annulation cascade. Org Lett 19:4948–4951

    Article  PubMed  CAS  Google Scholar 

  86. Gao YJ, Hider RC, Ma YM (2019) An efficient 3-acylquinoline synthesis from acetophenones and anthranil via C(sp3)–H bond activation mediated by selectfluor. RSC Adv 9:10340–10344

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  87. Xie CX, Zhang ZY, Li DY, Gong J, Han XS, Liu X, Ma C (2017) Dimethyl sulfoxide involved one-pot synthesis of quinoxaline derivatives. J Org Chem 82:3491–3499

    Article  PubMed  CAS  Google Scholar 

  88. Yuan J, Yu J-T, Jiang Y, Cheng J (2017) Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolones. Org Biomol Chem 15:1334–1337

    Article  PubMed  CAS  Google Scholar 

  89. Jadhav SD, Singh A (2017) Oxidative annulations involving DMSO and formamide: K2S2O8 mediated syntheses of quinolines and pyrimidines. Org Lett 19:5673–5676

    Article  PubMed  CAS  Google Scholar 

  90. Jiang T-S, Wang X, Zhang XL (2018) Synthesis of quinolines from anilines, acetophenones and DMSO under air. Tetrahedron Lett 59:2979–2982

    Article  CAS  Google Scholar 

  91. Yuan J, Li JB, Wang BB, Sun S, Cheng J (2017) Base-promoted formal [4+1+1] annulation of aldehyde, N-benzyl amidine and DMSO toward 2,4,6-triaryl pyrimidines. Tetrahedron Lett 58:4783–4785

    Article  CAS  Google Scholar 

  92. Liu YF, Hu YQ, Cao ZZ, Zhan X, Luo WP, Liu Q, Guo CC (2018) Copper-catalyzed aerobic oxidative cyclization of anilines, aryl methyl ketones and DMSO: efficient assembly of 2-arylquinolines. Adv Synth Catal 360:2691–2695

    Article  CAS  Google Scholar 

  93. Phanindrudu M, Wakade SB, Tiwari DK, Likhar PR, Tiwari DK (2018) Transition-metal-free approach for the synthesis of 4-arylquinolines from alkynes and anilines. J Org Chem 83:9137–9143

    Article  PubMed  CAS  Google Scholar 

  94. Zheng KL, Zhuang SY, Shu WM, Wu YD, Yang CL, Wu AX (2018) Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source. Chem Commun 54:11897–11900

    Article  CAS  Google Scholar 

  95. Xu XF, Yang YR, Zhang X, Yi W (2018) Direct synthesis of quinolines via Co(III)-catalyzed and DMSO-involved C−H activation/cyclization of anilines with alkynes. Org Lett 20:566–569

    Article  PubMed  CAS  Google Scholar 

  96. Zhang PQ, Yang YR, Chen ZY, Xu Z, Xu XF, Zhou Z, Yu XY, Yi W (2019) Cobalt(III)-catalyzed, DMSO-involved, and TFA-controlled regioselective C-H functionalization of anilines with alkynes for specific assembly of 3-arylquinolines. Adv Synth Catal 361:3002–3007

    Article  CAS  Google Scholar 

  97. Shu W-M, He J-X, Zhang X-F, Wang S, Wu A-X (2019) TFA-mediated DMSO-participant sequential oxidation/1,3-dipolar cycloaddition cascade of pyridinium ylides for the assembly of indolizines. J Org Chem 84:2962–2968

    Article  PubMed  CAS  Google Scholar 

  98. Shu W-M, Wang S, Zhang X-F, He J-X, Wu A-X (2019) A cascade oxidation/[4+1] annulation of sulfonium salts for synthesis of polyfunctional furans: DMSO as one carbon source. Org Biomol Chem 17:4311–4316

    Article  PubMed  CAS  Google Scholar 

  99. Lee S, Sim J, Jo H, Viji M, Srinu L, Lee K, Lee H, Manjunatha V, Jung J-K (2019) Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon. Org Biomol Chem 17:8067–8070

    Article  PubMed  CAS  Google Scholar 

  100. Jiang T-S, Zhou YH, Dai L, Liu XJ, Zhang XL (2019) Acid-promoted metal-free synthesis of 3-ketoquinolines from amines, enaminones and DMSO. Tetrahedron Lett 60:2078–2083

    Article  CAS  Google Scholar 

  101. Wakade SB, Tiwari DK, Phanindrudu M, Pushpendra, Tiwari DK (2019) Synthesis of 3-keto-quinolines from enaminones, anilines and DMSO: transition metal free one pot cascade. Tetrahedron 75:4024–4030

    Article  CAS  Google Scholar 

  102. Zhang Y, Ding YX, Chen RE, Ma YM (2020) One-pot cascade reaction for the synthesis of phenanthridines via suzuki coupling/C-H oxidation/aromatization. Adv Synth Catal 362:5697–5707

    Article  CAS  Google Scholar 

  103. Zhu XM, Zhang FX, Kuang DZ, Deng GB, Yang Y, Yu JX, Liang Y (2020) K2S as sulfur source and DMSO as carbon source for the synthesis of 2-unsubstituted benzothiazoles. Org Lett 22:3789–3793

    Article  PubMed  CAS  Google Scholar 

  104. Zhao P, Yu X-X, Zhou Y, Geng X, Wang C, Huang C, Wu Y-D, Zhu Y-P, Wu A-X (2020) Splitting methyl ketones into two parts: synthesis of 4(3H)-quinazolinones via consecutive cyclization/ring-opening reaction. Org Lett 22:7103–7107

    Article  PubMed  CAS  Google Scholar 

  105. Yadav P, Awasthi A, Gokulnath S, Tiwari DK (2021) DMSO as a methine source in TFA-mediated one-pot tandem regioselective synthesis of 3-substituted-1-Aryl-1H-pyrazolo-[3,4-b]quinolines from anilines and pyrazolones. J Org Chem 86:2658–2666

    Article  PubMed  CAS  Google Scholar 

  106. Ma J-T, Wang L-S, Chai Z, Chen X-F, Tang B-C, Chen X-L, He C, Wu Y-D, Wu A-X (2021) Access to 2-arylquinazolines via catabolism/reconstruction of amino acids with the insertion of dimethyl sulfoxide. Chem Commun 57:5414–5417

    Article  CAS  Google Scholar 

  107. Luo R, Guo LN, Liu WJ, Wang SH (2021) Copper-catalyzed synthesis of phenolic compounds with DMSO as the methylene source. Synth Commun 51:1712–1722

    CAS  Google Scholar 

  108. Zhang Y, Chen RE, Wang ZM, Wang L, Ma YM (2021) I2-catalyzed three-component consecutive reaction for the synthesis of 3-aroylimidazo[1,2-a]-N-heterocycles. J Org Chem 86:6239–6246

    Article  PubMed  CAS  Google Scholar 

  109. Wang AA, Liu XS, Kong Y, Wang J, Jiang T-S (2021) Substrate-induced DMSO activation and subsequent reaction for rapid construction of substituted pyrimidines. Org Chem Front 8:947–952

    Article  CAS  Google Scholar 

  110. Guo HJ, Tian LH, Liu YY, Wan J-P (2022) DMSO as a C1 source for [2+2+1] pyrazole ring construction via metal-free annulation with enaminones and hydrazines. Org Lett 24:228–233

    Article  PubMed  CAS  Google Scholar 

  111. Yang TL, Li H, Nie ZW, Su M-D, Luo W-P, Liu Q, Guo C-C (2022) [3+1+1+1] annulation to the pyridine structure in quinoline molecules based on DMSO as a nonadjacent dual-methine synthon: simple synthesis of 3-arylquinolines from arylaldehydes, arylamines, and DMSO. J Org Chem 87:2797–2808

    Article  PubMed  Google Scholar 

  112. Li J-Q, Tan H-L, Ma D-D, Zhu X-X, Cui H-L (2021) Formylation and bromination of pyrrolo[2,1-a]isoquinoline derivatives with bromoisobutyrate and dimethyl sulfoxide. J Org Chem 86:10118–10128

    Article  PubMed  CAS  Google Scholar 

  113. Bhattacharjee S, Laru S, Ghosh P, Hajra A (2021) Potassium persulfate mediated chemodivergent c-3 functionalization of 2H-indazoles with DMSO as C1 source. J Org Chem 86:10866–10873

    Article  PubMed  CAS  Google Scholar 

  114. Allard S, Forster M, Souharce B, Thiem H, Scherf U (2008) Organic semiconductors for solution-processable field-effect transistors (OFETs). Angew Chem Int Ed 47:4070–4098

    Article  CAS  Google Scholar 

  115. Mishra A, Ma C-Q, Bäuerle P (2009) Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. Chem Rev 109:1141–1276

    Article  PubMed  CAS  Google Scholar 

  116. Wang C, Dong H, Hu W, Liu Y, Zhu D (2012) Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics. Chem Rev 112:2208–2267

    Article  PubMed  CAS  Google Scholar 

  117. Liu H, He G-C, Zhao C-Y, Zhang X-X, Ji D-W, Hu Y-C, Chen Q-A (2021) Redox-divergent construction of (dihydro)thiophenes with DMSO. Angew Chem Int Ed 60:24284–24291

    Article  CAS  Google Scholar 

  118. Wang M, Xiang J-C, Cheng Y, Wu Y-D, Wu A-X (2016) Synthesis of 2,4,5-trisubstituted furans via a triple C(sp3)−H functionalization reaction using rongalite as the C1 unit. Org Lett 18:524–527

    Article  PubMed  Google Scholar 

  119. Dighe SU, Mukhopadhyay S, Priyanka K, Batra S (2016) Metal-free oxidative nitration of α-carbon of carbonyls leads to one-pot synthesis of thiohydroximic acids from acetophenones. Org Lett 18:4190–4193

    Article  PubMed  CAS  Google Scholar 

  120. An ZY, She Y, Yang XD, Pang XB, Yan RL (2016) Metal-free synthesis of 3-methylthiofurans from homopropargylic alcohols and DMSO via a tandem sulfenylation/cyclization reaction in a one-pot manner. Org Chem Front 3:1746–1749

    Article  CAS  Google Scholar 

  121. Hu L, Wang DD, Chen X, Yu L, Yu YQ, Tan Z, Zhu GG (2017) Copper-catalyzed decarboxylative methylthiolation of aromatic carboxylate salts with DMSO. Org Biomol Chem 15:5674–5679

    Article  PubMed  CAS  Google Scholar 

  122. Liu YF, Hu YQ, Cao ZZ, Zhan X, Luo WP, Liu Q, Guo CC (2019) Direct assembly of polysubstituted furans via C(sp3)–H bond functionalization by using dimethyl sulfoxide as a dual synthon. Adv Synth Catal 361:1084–1091

    Article  CAS  Google Scholar 

  123. He RF, Chen XW, Li YB, Liu Q, Liao CS, Chen L, Huang YB (2019) NH4I-promoted and H2O-controlled intermolecular Bis-sulfenylation and hydroxysulfenylation of alkenes via a radical process. J Org Chem 84:8750–8758

    Article  PubMed  CAS  Google Scholar 

  124. Xiao Y, Wang S, Liu JY, Zhang H, Xu YN (2019) Copper(II) mediated C-H methylthiolation of 2-phenyl pyridines with dimethyl sulfoxide using an amino acid ligand. Tetrahedron Lett 60:1317–1320

    Article  CAS  Google Scholar 

  125. Lu L-H, Ou GC, Zhao XJ, Wang YF, Chen XL, Liao WJ, Li SD, Wu C (2021) Selective difunctionalization of electron-deficient alkynes: access to (E)-2-iodo-3-(methylthio)acrylate. Org Biomol Chem 19:8128–8132

    Article  PubMed  CAS  Google Scholar 

  126. Zhang L-Y, Wu Y-H, Wang N-X, Gao X-W, Yan Z, Xu B-C, Liu N, Wang B-Z, Xin YL (2021) Methylthiolation for electron-rich heteroarenes with DMSO-TsCl. Eur J Org Chem 2021:1446–1451

    Article  CAS  Google Scholar 

  127. Zhang BB, Li XX, Li XM, Sun FX, Du YF (2021) Synthesis of 3-methylthio-benzo[b]furans/thiophenes via intramolecular cyclization of 2-alkynylanisoles/sulfides mediated by DMSO/DMSO-d6 and SOCl2. Chin J Chem 39:887–895

    Article  Google Scholar 

  128. Li XX, Wang YX, Ouyang YX, Yu ZY, Zhang BB, Zhang JR, Shi HF, Zuilhof H, Du YF (2021) Unexpected substituent effects in spiro-compound formation: steering N-aryl propynamides and DMSO toward site-specific sulfination in quinolin-2-ones or spiro[4,5]trienones. J Org Chem 86:9490–9502

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  129. Pramanik MMD, Rastogi N (2016) Visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO. Chem Commun 52:8557–8560

    Article  CAS  Google Scholar 

  130. Shao AL, Gao M, Chen ST, Wang T, Lei AW (2017) CO/O2 assisted oxidative carbon-carbon and carbon-heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins. Chem Sci 8:2175–2178

    Article  PubMed  CAS  Google Scholar 

  131. Huang M-H, Zhu C-F, He C-L, Zhu Y-L, Hao W-J, Wang D-C, Tu S-J, Jiang B (2018) Visible-light-induced methylsulfonylation/bicyclization of C(sp3)-tethered 1,7-enynes using a DMSO/H2O system. Org Chem Front 5:1643–1650

    Article  CAS  Google Scholar 

  132. Zhang J, Cheng SJ, Cai ZQ, Liu P, Sun PP (2018) Radical addition cascade cyclization of 1,6-enynes with DMSO to access methylsulfonylated and carbonylated benzofurans under transition-metal-free conditions. J Org Chem 83:9344–9352

    Article  PubMed  CAS  Google Scholar 

  133. Zhao P, Wu X, Geng X, Wang C, Zhou Y, Wu Y-D, Wu A-X (2019) I2/PhI(OAc)2 copromoted amination reaction: synthesis of α-dicarbonylsulfoximine derivatives by incorporating an intact dimethyl sulfoxide. J Org Chem 84:8322–8329

    Article  PubMed  CAS  Google Scholar 

  134. Zhou P, Pan YP, Tan H, Liu WB (2019) I2−DMSO−H2O: a metal-free combination system for the oxidative addition of alkynes to access (E)-α-iodo-β-methylsulfonylalkenes. J Org Chem 84:15662–15668

    Article  PubMed  CAS  Google Scholar 

  135. Fu D, Dong J, Du HG, Xu JX (2020) Methanesulfinylation of benzyl halides with dimethyl sulfoxide. J Org Chem 85:2752–2758

    Article  PubMed  CAS  Google Scholar 

  136. Liu YF, Zhan X, Ji PY, Xu JW, Liu Q, Luo WP, Chen TQ, Guo CC (2017) Transition metal-free C(sp3)–H bond coupling among three methyl groups. Chem Commun 53:5346–5349

    Article  CAS  Google Scholar 

  137. Xing HT, Chen L, Jia YM, Jiang ZX, Yang ZG (2017) Fe2O3-catalyzed Pummerer rearrangement of acyl chlorides and sulfoxides: facile synthesis of alkylthiomethyl ester. Tetrahedron Lett 58:2199–2202

    Article  CAS  Google Scholar 

  138. Wang SL, Fu ZJ, Jiang YQ, Liang YX, Cai H (2019) Facile synthesis of methylthiomethyl esters through Pummerer-type rearrangement of carboxylic acids and DMSO under metal-free conditions. Synth Commun 49:950–958

    Article  CAS  Google Scholar 

  139. Zhang Y, Zhou DH, Ma YM, Chen J (2020) DMSO-mediated synthesis of methylene-bridged unsymmetrical bisamides in the presence of AcOH. Synthesis 52:297–303

    Article  CAS  Google Scholar 

  140. Wang AA, Feng YY, Li S, Shi X, Jiang T-S (2022) Oxidant-free selective synthesis of functionalized chroman-4-ones from ortho-hydroxyacetophenones under HOAc/DMSO conditions. Synthesis 54:2185–2192

    Article  CAS  Google Scholar 

  141. Li J-Q, Chen X-H, Cui H-L (2022) Modification of pyrrolo[2,1-a]isoquinolines and pyrrolo[1,2-a]quinolines with ammonium acetate and dimethyl sulfoxide via methylthiomethylation. J Org Chem 87:2421–2434

    Article  PubMed  Google Scholar 

  142. Wen ZK, Liu X-H, Liu Y-F, Chao J-B (2017) Acid promoted direct cross-coupling of methyl ketones with dimethyl sulfoxide: access to ketoallyl methylsulfides and –sulfones. Org Lett 19:5798–5801

    Article  PubMed  CAS  Google Scholar 

  143. Chang M-Y, Chen H-Y, Tsai Y-L (2019) NH2OH−HCl-mediated umpolung α-methylsulfonylation of α-sulfonyl ketones with methylsulfoxides: synthesis of α,β-bissulfonyl arylketones. Org Lett 21:1832–1836

    Article  PubMed  CAS  Google Scholar 

  144. Wu Y, Zhang MS, Zhang YL, Li MY, Feng WS, Zheng XK, Tang L (2020) NBS-activated cross-dehydrogenative esterification of carboxylic acids with DMSO. Org Chem Front 7:2719–2724

    Article  CAS  Google Scholar 

  145. Fan J, Zhao YM, Zhang JT, Xie MH, Zhang YZ (2020) Acid-controlled access to β-sulfenyl ketones and α,β-disulfonyl ketones by pummerer reaction of β-keto sulfones and sulfoxides. J Org Chem 85:691–701

    Article  PubMed  CAS  Google Scholar 

  146. Rohe S, Révol G, Marmin T, Barriault D, Barriault L (2020) Single-electron transfer from dimsyl anion in the alkylation of phenols. J Org Chem 85:2806–2813

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank the Natural Science Foundation of China (nos. 21676076, 21878071, and 21971060), the Hu-Xiang High Project of Hunan Province (2018RS3042), and the Recruitment Program for Foreign Experts of China (WQ20164300353) for financial support.

Author information

Authors and Affiliations

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China

    Hao Lu, Zhou Tong, Lifen Peng, Zhiqing Wang, Shuang-Feng Yin, Nobuaki Kambe & Renhua Qiu

  2. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, 565-0871, Japan

    Nobuaki Kambe

  3. Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201, Hunan, China

    Lifen Peng

Authors
  1. Hao Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhou Tong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lifen Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zhiqing Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Shuang-Feng Yin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Nobuaki Kambe
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Renhua Qiu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Renhua Qiu.

Ethics declarations

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lu, H., Tong, Z., Peng, L. et al. Recent Advances in the Use of Dimethyl Sulfoxide as a Synthon in Organic Chemistry. Top Curr Chem (Z) 380, 55 (2022). https://doi.org/10.1007/s41061-022-00411-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-022-00411-8

Keywords

Search

Navigation