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Synthesis of β-Halofurans

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Halogenated Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 27))

Abstract

Furans substituted with halogens at the beta carbon, which is less prone to electrophilic reactions compared to an alpha position, are important intermediates for accessing highly substituted furans. The regioselectivity of the introduction of a halogen plays an important role in their preparation. This review summarizes efforts for the synthesis of β-halofurans (but not benzofurans) as sorted by halogen (iodo, bromo, chloro, and fluoro). This article provides general reaction schemes that were confirmed with multiple examples and are sometimes applicable to other halogens, and selected reactions specific to a particular substrate and a halogen.

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Abbreviations

Ac:

Acetyl

aq:

Aqueous

Ar:

Aryl

Bn:

Benzyl

bpy:

2,2′-Bipyridyl

Bu:

Butyl

cat:

Catalyst

DCE:

1,2-Dichloroethane

DDQ:

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DME:

1,2-Dimethoxyethane

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

equiv:

Equivalent

Et:

Ethyl

i-Pr:

Iso-propyl

KHMDS:

Potassium hexamethyldisilazide

LDA:

Lithium diisopropylamide

Me:

Methyl

mol:

Mole(s)

NBS:

N-bromosuccinimide

NCS:

N-chlorosuccinimide

NIS:

N-iodosuccinimide

NMR:

Nuclear magnetic resonance

Nu:

Nucleophile

NXS:

N-halosuccinimide

Ph:

Phenyl

PPTS:

Pyridinium p-toluensulfonate

rt:

Room temperature

s-Bu:

Sec-butyl

TBDMS:

Tert-butyldimethylsilyl

TBDPS:

Tert-butyldiphenylsilyl

t-Bu:

Tert-butyl

THF:

Tetrahydrofuran

THP:

Tetrahydropyran-2-yl

TMEDA:

N,N,N′,N′-tetramethyl-1,2-ethylenediamine

TMP:

Tetramethylpiperidyl

Tol:

4-Methylphenyl

References

  1. Graening T, Thrun F (2008) Furans and their benzo derivatives: synthesis. In: Katritzky AR (ed) Comprehensive heterocyclic chemistry III, vol 3. Elsevier, New York, pp 497–569

    Chapter  Google Scholar 

  2. König B (2001) Product class 9: furans. In: Maas G (ed) Hetarenes and related ring systems; science of synthesis, vol 9. George Thieme Verlag, Germany, pp 183–286, Chap. 9.9

    Google Scholar 

  3. Yeung K-S, Yang Z, Peng X-S, Hou X-L (2011) Five-membered ring systems: furans and benzofurans. In: Gribble G, Joule JA (eds) Progress in heterocyclic chemistry, vol 22. Elsevier, New York, pp 181–216, Chap. 5.3

    Google Scholar 

  4. Arimitsu S, Jacobsen JM, Hammond GB (2008) Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols. J Org Chem 73:2886–2889. doi:10.1021/jo800088y

    Article  CAS  Google Scholar 

  5. Hussain M, Khera RA, Hung NT, Langer P (2011) Site-selective Suzuki–Miyaura cross-coupling reactions of 2,3,4,5-tetrabromofuran. Org Biomol Chem 9:370–373. doi:10.1039/C0OB00695E

    Article  CAS  Google Scholar 

  6. Schweizer SA, Bach T (2010) Regioselective Pd(0)-Catalyzed Hiyama Cross-Coupling Reactions at Dihalo-Substituted Heterocycles. Synlett 81–84. doi:10.1055/s-0029-1218528

    Google Scholar 

  7. Karpov AS, Merkul E, Oeser T, Müller TJJ (2006) One-Pot three-component synthesis of 3-halofurans and 3-chloro-4-iodofurans. Eur J Org Chem 2991–3000. doi:10.1002/ejoc.200600225

  8. Sniady A, Morreale MS, Wheeler KA, Dembinski R (2008) Room-temperature electrophilic 5-endo-dig chlorocyclization of Alk-3-yn-1-ones with the use of pool sanitizer: synthesis of 3-chlorofurans and 5-chlorofuropyrimidine nucleosides. Eur J Org Chem 3449–3452. doi:10.1002/ejoc.200890051

  9. a) Cho C-H, Larock RC (2011) Highly Substituted Lactone/Ester-Containing Furan Library by the Palladium-Catalyzed Carbonylation of Hydroxyl-Substituted 3-Iodofurans. ACS Comb Sci 13:272–279. doi:10.1021/co100088q. b) Sauers RR, Van Arnum SD (2004) γ-Hydroxyalkynyl ketones as useful scaffolds for the preparation of combinatorial libraries of furans, isoxazoles and pyrazoles. J Comb Chem 6:350–355. doi:10.1021/cc030029

    Article  CAS  Google Scholar 

  10. Webster R, Lautens M (2009) Conformational effects in diastereoselective aryne Diels-alder reactions: synthesis of benzo-fused [2.2.1] Heterobicycles. Org Lett 11:4688–4691. doi:10.1021/ol9019869

    Article  CAS  Google Scholar 

  11. Pieniazek SN, Houk KN (2006) The origin of the halogen effect on reactivity and reversibility of Diels-alder cycloadditions involving furan. Angew Chem Int Ed 45:1442–1445. doi:10.1002/anie.200502677

    Article  CAS  Google Scholar 

  12. Morton GE, Barrett AGM (2005) 1,4-Difluoro-2,5-dimethoxybenzene as a precursor for iterative double benzyne-furan Diels–Alder reactions. J Org Chem 70:3525–3529. doi:10.1021/jo050112e

    Article  CAS  Google Scholar 

  13. Milkiewicz KL, Neagu IB, Parks DJ, Lu T (2003) Synthesis of a novel series of 10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-en-4-ones through an intramolecular Diels-Alder reaction. Tetrahedron Lett 44:7341–7343. doi:10.1016/S0040-4039(03)01865-3

    Article  CAS  Google Scholar 

  14. Ram NR, Kumar N (2008) Synthesis of highly substituted m-chlorophenolic biaryls by chlorine substituent-promoted Diels–Alder reaction of 2-aryl-3-chlorofurans. Tetrahedron 64:10267–10271. doi:10.1016/j.tet.2008.07.050

    Article  CAS  Google Scholar 

  15. Young IS, Kerr MA (2007) Total synthesis of (+)-nakadomarin a. J Am Chem Soc 129:1465–1469. doi:10.1021/ja068047t

    Article  CAS  Google Scholar 

  16. Bach T, Krüger L (1999) The preparation of 2,3,5-Tri- and 2,3-disubstituted furans by regioselective palladium(0)-catalyzed coupling reactions: application to the syntheses of rosefuran and the F5 furan fatty acid. Eur J Org Chem 2045–2057. doi:10.1002/(SICI)1099-0690(199909)1999:9<2045::AID-EJOC2045>3.0.CO;2-6

    Google Scholar 

  17. König, B. Product Class 9: Furans. In Hetarenes and Related Ring Systems; Science of Synthesis; Maas, G., Ed.; George Thieme Verlag: Stuttgart, Germany, 2001; Vol. 9, Ch. 9.9.4.1.12. p 249–252.

    Google Scholar 

  18. Serdyuk O, Butin A, Abaev V (2010) Synthesis of fluorofurans and perfluoroalkylfurans. J Fluorine Chem 131:296–319. doi:10.1016/j.jfluchem.2009.11.009

    Article  CAS  Google Scholar 

  19. Carpenter AJ, Chadwick DJ (1985) Dimetallations of 2-substituted furans and thiophenes: approaches to the 2, 3, 5-trisubstituted heterocycles. Tetrahedron Lett 26:5335–5338. doi:10.1016/S0040-4039(00)95032-9

    Article  CAS  Google Scholar 

  20. Bures E, Nieman JA, Yu S, Spinazzé PG, Bontront J-LJ, Hunt IR, Rauk A, Keay BA (1997) Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 2. Regioselective Lithiation of 2-Silylated-3-substituted Furan Rings. J Org Chem 62:8750–8759 and references cited therein. doi:10.1021/jo971098b

    Google Scholar 

  21. Song ZZ, Wong HNC (1994) 3,4-Disubstituted Furans, 5. Regiospecific Mono-ipso-Iodination of 3,4-Bis(trimethylsilyl)furan and Regiospecific ipso-Iodination of Tris[(4-alkyl- or -aryl)furan-3-yl]boroxines to 4-Substituted 3-(Trimethylsilyl)furans and Unsymmetrical 3,4-Disubstituted Furans. Liebigs Ann Chem:29–34

    Google Scholar 

  22. Lopez FJ, Jett M-F, Muchowski JM, Nitzan D, O’Yang C (2002) Synthesis and biological evaluation of ketorolac analogs. Heterocycles 56:91–95. doi:10.3987/COM-01-S(K)44

    Article  CAS  Google Scholar 

  23. Sniady A, Wheeler KA, Dembinski R (2005) 5-Endo-Dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones: regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans. Org Lett 7:1769–1772. doi:10.1021/ol050372i

    Article  CAS  Google Scholar 

  24. Sniady A, Morreale MS, Dembinski R (2007) Electrophilic cyclization with N-Iodosuccinimide: Preparation of 5-(4-bromophenyl)-3-iodo-2-(4-methylphenyl)furan. Org Synth 84:199–208; Coll 11:794-801 (2009). doi:10.1002/0471264229.os084.20

    Google Scholar 

  25. Li Y, Gundapuneni D, Sniady A, Morreale MS, Marcinek A, Wheeler KA, Dembinski R, manuscript in preparation

    Google Scholar 

  26. Li Y, Wheeler KA, Dembinski R (2011) Electrophilic cyclizations of 2-fluoroalk-3-yn-1-ones: room-temperature synthesis of diversely 2,5-disubstituted 3,4-fluorohalofurans. Eur J Org Chem 2767–2771. doi:10.1002/ejoc.201100344

  27. Chen Z, Huang G, Jiang H, Huang H, Pan X (2011) Synthesis of 2,5-disubstituted 3-iodofurans via palladium-catalyzed coupling and iodocyclization of terminal alkynes. J Org Chem 76:1134–1139. doi:10.1021/jo1023987

    Article  CAS  Google Scholar 

  28. Marshall JA, Wolf MA (1996) Amination, aminocarbonylation, and alkoxycarbonylation of allenic/propargylic Pd intermediates derived from nonracemic propargylic mesylates: synthesis of nonracemic propargyl amines, allenic amides, and butenolides. J Org Chem 61:3238–3239. doi:10.1021/jo960442m

    Article  CAS  Google Scholar 

  29. Yao T, Zhang X, Larock RC (2005) Synthesis of highly substituted furans by the electrophile-induced coupling of 2-(1-Alkynyl)-2-alken-1-ones and nucleophiles. J Org Chem 70:7679–7685. doi:10.1021/jo0510585

    Article  CAS  Google Scholar 

  30. Liu Y, Zhou S (2005) Electrophilic cylization of 2-(1-alkynyl)-2-alken-1-ones using the I2/K3PO4 system: an efficient synthesis of highly substituted iodofurans. Org Lett 7:4609–4611. doi:10.1021/ol051659i

    Article  CAS  Google Scholar 

  31. Huang X, Fu W, Miao M (2008) An efficient synthesis of highly substituted furans via the electrophilic cyclization of 1-(1-alkynyl)-cyclopropyl ketones. Tetrahedron Lett 49:2359–2362. doi:10.1016/j.tetlet.2008.02.081

    Article  CAS  Google Scholar 

  32. Xie Y-X, Liu X-Y, Wu L-Y, Han Y, Zhao L-B, Fan M-J, Liang Y-M (2008) Efficient synthesis of substituted 3-iodofurans by electrophilic cyclization of propargylic oxirane derivatives. Eur J Org Chem 1013–1018. doi:10.1002/ejoc.200700963

  33. Yoshida M, Al-Amin M, Matsuda K, Shishido K (2008) Synthesis of substituted furans by platinum-catalyzed cyclization of propargylic oxiranes in aqueous media Tetrahedron Lett 49:5021–5023. doi:10.1016/j.tetlet.2008.06.043

    CAS  Google Scholar 

  34. Yoshida M, Al-Amin M, Shishido K (2009) Syntheses of substituted furans and pyrroles by platinum-catalyzed cyclizations of propargylic oxiranes and aziridines in aqueous media. Synthesis:2454–2466. doi:10.1055/s-0029-1216867

    Google Scholar 

  35. Zhou H, Yao J, Liu G (2008) Electrophilic cyclization of 4-thio-but-2-yn-1-ols via 1,2-migration of the thio group: efficient synthesis of 2,4-dihalo-3-thio-substituted furans. Tetrahedron Lett 49:226–228. doi:10.1016/j.tetlet.2007.11.092

    Article  CAS  Google Scholar 

  36. Obrecht D (1989) Acid-catalyzed cyclization reactions of substituted acetylenic ketones: a new approach for the synthesis of 3-halofurans, flavones, and styrylchromones. Helv Chim Acta 72:447–456. doi:10.1002/hlca.19890720305

    Article  CAS  Google Scholar 

  37. Karpov AS, Merkul E, Oeser T, Müller TJJ (2005) A novel one-pot three-component synthesis of 3-halofurans and sequential Suzuki coupling. Chem Commun 2581–2583. doi:10.1039/B502324F

  38. Yang F, Jin T, Bao M, Yamamoto Y (2011) Facile synthesis of 3,4-dihalofurans via electrophilic iodocyclization. Chem Commun 47:4541–4543. doi:10.1039/C1CC10584A

    Article  CAS  Google Scholar 

  39. Ji K-G, Zhu H-T, Yang F, Shaukat A, Xia X-F, Yang Y-F, Liu X-Y, Liang Y-M (2010) Synthesis of five- and six-membered dihalogenated heterocyclic compounds by electrophile-triggered cyclization. J Org Chem 75:5670–5678. doi:10.1021/jo101085f

    Article  CAS  Google Scholar 

  40. Reich HJ, Olson RE (1987) Preparation of 3-Substituted 4-Methylfurans: 3-Iodo-4-methyl- and 3-Formyl-4-methylfuran. J Org Chem 52:2315–2317. doi:10.1021/jo00387a043

    Article  CAS  Google Scholar 

  41. Schultz-Fademrecht C, Zimmermann M, Fröhlich R, Hoppe D (2003) Synthesis of enantiopure 2,5-dihydro-3-iodofurans and substituted 3-iodofurans by iodocyclization of 4-hydroxy-1,2-alkadienyl carbamates. Synlett:1969–1972. doi:10.1055/s-2003-42046

    Google Scholar 

  42. Bew SP, Knight DW (1996) A brief synthesis of β-iodofurans. Chem Commun 1007–1008. doi:10.1039/CC9960001007

  43. El-Taeb GMM, Evans AB, Jones S, Knight DW (2001) Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols. Tetrahedron Lett 42:5945–5948. doi:10.1002/ejoc.200700681

    Article  CAS  Google Scholar 

  44. Bew SP, El-Taeb GMM, Jones S, Knight DW, Tan W-F (2007) Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations. Eur J Org Chem 5759–5770. doi:10.1002/ejoc.200700681

  45. Evans AB, Flügge S, Jones S, Knight DW, Tan W-F (2008) A new synthesis of the F5 furan fatty acid and a first synthesis of the F6 furan fatty acid. Arkivoc 10:95–102

    Google Scholar 

  46. Wen S, Liu W, Liang Y (2007) Convenient synthesis of polysubstituted 3-iodofurans through the tandem ring-opening/cyclization reaction of 1-Alkynyl-2,3-epoxy Alcohols. Synthesis:3295–3300. doi:10.1055/s-2007-990830

    Google Scholar 

  47. Tseng J-C, Chen J-H, Luh T-Y (2006) A Convenient Synthesis of Tetrasubstituted Furans from Propargylic Dithioacetals. Synlett:1209–1212. doi:10.1055/s-2006-939686

    Google Scholar 

  48. Chen C-W, Luh T-Y (2009) Mercuric acetate-mediated annulation of homopropargylic alcohols having thioether substituent. A general route for the synthesis of tetrasubstituted furans from propargylic dithioacetals Tetrahedron Lett 50:3263–3265. doi:10.1016/j.tetlet.2009.02.043

    CAS  Google Scholar 

  49. Sromek AW, Rubina M, Gevorgyan V (2005) 1,2-halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans. J Am Chem Soc 127:10500–10501. doi:10.1021/ja053290y

    Article  CAS  Google Scholar 

  50. Dudnik AS, Sromek AW, Rubina M, Kim JT, Kel’in AV, Gevorgyan V (2008) Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles. J Am Chem Soc 130:1440–1452. doi:10.1021/ja0773507

    Article  CAS  Google Scholar 

  51. Pevzner LM (2009) Synthesis of isomeric bromo(diethoxyphosphorylmethyl)furans. Russ J Gen Chem 79:362–372. doi:10.1134/S1070363209030050 (Zh Obshch Khim 2009, 79:372-382

    Article  CAS  Google Scholar 

  52. Rees CW, Yue T-Y (1997) Further reactions of furans with trithiazyl trichloride; mechanistic considerations. J Chem Soc Perkin Trans 1:2247–2252. doi:10.1039/A700488E

    Article  Google Scholar 

  53. Milkiewicz KL, Parks DJ, Lu T (2003) Synthesis of a novel series of tetra-substituted furan[3,2-b]pyrroles. Tetrahedron Lett 44:4257–4260. doi:10.1016/S0040-4039(03)00895-5

    Article  CAS  Google Scholar 

  54. Yin G, Wang Z, Chen A, Gao M, Wu A, Pan Y (2008) A new facile approach to the synthesis of 3-methylthio-substituted furans, pyrroles, thiophenes, and related derivatives. J Org Chem 73:3377–3383. doi:10.1021/jo702585s

    Article  CAS  Google Scholar 

  55. Wang X, Liu LY, Chang WX, Li J (2009) Sonogashira coupling reaction of homopropargyl ether with aryl bromides and synthesis of 2,5-disubstituted 3-bromofurans. Sci China Ser B-Chem 52:1314–1320. doi:10.1007/s11426-009-0203-z

    Article  CAS  Google Scholar 

  56. Fuganti C, Serra S (1998) A new approach to 2-aryl-7-alkoxy-benzofurans: synthesis of ailanthoidol, a natural neolignan. Tetrahedron Lett 39:5609–5610. doi:10.1016/S0040-4039(98)01053-3

    Article  CAS  Google Scholar 

  57. Toro A, Deslongchamps P (2003) Furanophane transannular Diels−Alder approach to (+)-chatancin: an asymmetric total synthesis of (+)-anhydrochatancin. J Org Chem 68:6847–6852. doi:10.1021/jo034123o

    Article  CAS  Google Scholar 

  58. Gorzynski M, Rewicki D (1986) Synthese von alkyl-2,3-dihydrothieno[2,3-c]furanen. Aromastoffen des Kaffees Liebigs Ann Chem 625–637. doi:10.1002/jlac.198619860404

  59. Alvarez-Ibarra C, Quiroga ML, Toledano E (1996) Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran. Tetrahedron 52:4065–4078. doi:10.1016/S0040-4020(96)00069-5

    Article  CAS  Google Scholar 

  60. Kabir SM, Miura M, Sasaki S, Harada G, Kuwatani Y, Yoshida M, Iyoda M (2000) New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization. Heterocycles 52:761–774. doi:10.3987/COM-99-S86

    Article  CAS  Google Scholar 

  61. Frohlich J, Hametner C (1996) Synthesis of trisubstituted furans from 2-bromo-5-methylfuran via halogen migrations and their selective preventions. Monatsh Chem 127:435–443. doi:10.1007/BF00810886

    Article  Google Scholar 

  62. Schlessinger RH, Pettus TRR, Springer JP, Hoogsteen K (1994) Diastereoselective Diels–Alder reactions using furan substituted with a nonracemic amine. J Org Chem 59:3246–3247. doi:10.1021/jo00091a002

    Article  CAS  Google Scholar 

  63. Xia Y, Dudnik AS, Gevorgyan V, Li Y (2008) Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity. J Am Chem Soc 130:6940–6941

    Article  CAS  Google Scholar 

  64. Yoshimura F, Takahashi M, Tanino K, Miyashita M (2009) An efficient synthetic method for 3-bromofuran derivatives via stereoselective cyclization of γ, δ-epoxy (E)-α-bromoacrylates. Heterocycles 77:201–206. doi:10.3987/COM-08-S(F)25

    Article  CAS  Google Scholar 

  65. Tanabe Y, Wakimura K, Nishii Y, Muroya Y (1996) Synthesis of 2,5-Diaryl-3-halofurans via Regioselective Ring Cleavage of Aryl 3-Aryl-2,2-dihalocyclopropyl Ketones. Synthesis:388–392. doi:10.1055/s-1996-4218

    Google Scholar 

  66. Batanero B, Vago M, Barba F (2000) Electrochemical synthesis of 5-amino-4-benzoyl-3-phenylfuran-2-carbonitrile. Heterocycles 53:1337–1342. doi:10.3987/COM-99-8843

    Article  CAS  Google Scholar 

  67. Lukevics E, Ignatovich L, Goldberg Y, Polyak F, Gauhkman A, Rozite S, Popelis J (1988) Reactions of trialkyl(2-furyl)germanes with electrophilic reagents. J Organomet Chem 348:11–23. doi:10.1016/0022-328X(88)80334-6

    Article  CAS  Google Scholar 

  68. Basarab GS, Hill PJ, Rastagar A, Webborn PJH (2008) Design of helicobacter pylori glutamate racemase inhibitors as selective antibacterial agents: a novel pro-drug approach to increase exposure. Bioorg Med Chem Lett 18:4716–4722. doi:10.1016/j.bmcl.2008.06.092

    Article  CAS  Google Scholar 

  69. Piller FM, Knochel P (2011) Regio- and chemoselective synthesis of fully substituted furans. Synthesis 1751–1758. doi:10.1055/s-0030-1260035

  70. Zhang HZ, Kasibhatla S, Kuemmerle J, Kemnitzer W, Mason KO, Qiu L, Grundy CC, Tseng B, Drewe J, Cai SX (2005) Discovery and structure-activity relationship of 3-aryl-5-aryl-1,2,4-oxadiazoles as a New series of apoptosis inducers and potential anticancer agents. J Med Chem 48:5215–5223. doi:10.1021/jm050292k

    Article  CAS  Google Scholar 

  71. Jones AM, Simpson AJ, Stanforth SP (1990) Synthesis of tetra-substituted furan derivatives from 1-arylpropane-2,3-diones. J Heterocycl Chem 27:1843–1844. doi:10.1002/jhet.5570270662

    Article  CAS  Google Scholar 

  72. Chauvin R (1995) “Carbomers”. II. En route to [C,C]6Carbo-benzene. Tetrahedron Lett 36:401–404. doi:10.1016/0040-4039(94)02276-H

    Article  CAS  Google Scholar 

  73. Lie Ken Jie MSF, Lau MML, Lam CNW (2003) Synthesis of novel Tri- and tetrasubstituted C18 furan fatty esters. Lipids 38:1293–1297. doi:10.1007/s11745-003-1192-8

    Article  Google Scholar 

  74. Claus H, Schäfer HJ (1985) 3,3-Dichlorotetrahydrofurans by reductive addition of 3-bromo 1,1,1-trichloroalkanes to carbonyl compounds. Tetrahedron Lett 26:4899–4902. doi:10.1016/S0040-4039(00)94980-3

    Article  CAS  Google Scholar 

  75. Ram RN, Kumar N (2008) Synthesis of 2,4-disubstituted 3-chlorofurans and the effect of the chlorine substituent in furan Diels–Alder reactions. Tetrahedron Lett 49:799–802. doi:10.1016/j.tetlet.2007.11.193

    Article  CAS  Google Scholar 

  76. Ram NR, Charles I (1999) Synthesis of 3-substituted and 2,3-disubstituted 4-chlorofurans. Chem Commun 2267–2268. doi:10.1039/A907270E

  77. Ram RN, Charles I (2008) Unexpected aromatization of 2-acetoxy-3,3-dichloro-4-(a-chloroalkyl)tetrahydrofurans to 3-alkyl-4-chlorofurans with NaI/DMF. Synth Commun 38:1946–1951. doi:10.1080/00397910801997678

    Article  CAS  Google Scholar 

  78. Dvornikova E, Bechcicka M, Kamieńska-Trela K, Krówczyński A (2003) Synthesis and NMR studies of 2- and 3-fluorosubstitued five-membered heterocycles. J Fluorine Chem 124:159–168. doi:10.1016/j.jfluchem.2003.07.001

    Article  CAS  Google Scholar 

  79. Li Y, Wheeler KA, Dembinski R (2010) Gold(I)-catalyzed cycloisomerization of 2-fluoroalk-3-yn-1-ones: synthesis of 2,5-substituted 3-fluorofurans. Adv Synth Catal 352:2761–2766. doi:10.1002/adsc.201000411

    Article  CAS  Google Scholar 

  80. Li Y, Wheeler KA, Dembinski R Room Temperature Syntheses of Entirely Diverse Substituted β-Fluorofurans. Org Biomol Chem doi: 10.1039/c1ob06693e

    Google Scholar 

  81. Li P, Gu J-W, Ying Y, He Y-M, Zhang H-F, Zhao G, Zhu S-Z (2010) Palladium-catalyzed alkenylation of fluoro-substituted furans via C–H activation to form tetrasubstituted furans. Tetrahedron 66:8387–8391. doi:10.1016/j.tet.2010.08.064

    Article  CAS  Google Scholar 

  82. Li P, Chai Z, Zhao G, Zhu S-Z (2009) Pd-catalyzed direct arylation of 3-fluorofurans utilizing the neighboring effect of fluorine atom: facile synthesis of tetrasubstituted monofluoro furans. Tetrahedron 65:1673–1678. doi:10.1016/j.tet.2008.12.026

    Article  CAS  Google Scholar 

  83. Li P, Chai Z, Zhao G, Zhu S-Z (2008) Synthesis of 3-fluoro-2,5-disubstituted furans and further derivative reactions to access fluorine-containing 3,3’-bifurans and tetrasubstituted furans. Synlett:2547–2551. doi:10.1055/s-2008-1078053

    Google Scholar 

  84. Sham HL, Betebenner DA (1991) A new and concise synthesis of 3-fIuoro-2,5-disubstituted furans. Chem Commun 1134–1135. doi:10.1039/C39910001134

  85. Arimitsu S, Hammond GB (2007) Selective synthesis of fluorinated furan derivatives via AgNO3-catalyzed activation of an electronically deficient triple bond. J Org Chem 72:8559–8561. doi:10.1021/jo701616c

    Article  CAS  Google Scholar 

  86. Hodge P, Derenberg M (1971) Reaction of difluorocarbene with 2-benzylidenecyclohexanones to afford phenylfluorofurans. J Chem Soc D Chem Commun 233–234. doi:10.1039/C29710000233

  87. Xu W, Chen Q-Y (2003) A novel approach of cycloaddition of difluorocarbene to α, β-unsaturated aldehydes and ketones: synthesis of gem-difluorocyclopropyl ketones and 2-fluorofurans. Org Biomol Chem 1:1151–1156. doi:10.1039/B212232D

    Article  CAS  Google Scholar 

  88. a) Pomeisl K, Kvíčala J, Paleta O (2006) Convenient synthesis of 3-fluoro-4,5-diphenylfuran-2(5H)-one from benzoin ethers. Novel and efficient Z-E isomerisation and cyclisation of 2-fluoroalkenoate precursors, substitution of vinylic fluorine. J Fluorine Chem 127:1390–1397. doi:10.1016/j.jfluchem.2006.05.012. b) Pomeisl K, Čejka J, KvÚčala J, Paleta O (2007) Synthesis of 3-Fluorofuran-2(5H)-ones Based on Z/E Photoisomerisation and Cyclisation of 2-Fluoro-4-hydroxybut-2-enoates. Eur J Org Chem:5917–5925. doi:10.1002/ejoc.200700439

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Oakland University, 2200 N. Squirrel Rd, Rochester, MI, 48309-4477, USA

    Roman Dembinski, Yan Li, Deepthi Gundapuneni & Alicia Decker

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  1. Roman Dembinski
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  2. Yan Li
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  3. Deepthi Gundapuneni
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  4. Alicia Decker
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Correspondence to Roman Dembinski .

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  1. , Department of Physical and Organic Chemi, "Jozef Stefan" Institute, Jamova 39, Ljubljana, 1000, Slovenia

    Jernej Iskra

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Dembinski, R., Li, Y., Gundapuneni, D., Decker, A. (2011). Synthesis of β-Halofurans. In: Iskra, J. (eds) Halogenated Heterocycles. Topics in Heterocyclic Chemistry, vol 27. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_57

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