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

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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.

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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

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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.

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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

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