Synthesis 2016; 48(10): 1421-1436
DOI: 10.1055/s-0035-1560429
review
© Georg Thieme Verlag Stuttgart · New York

Dimethyl Sulfoxide as a Synthon in Organic Chemistry

Ebenezer Jones-Mensah
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA   Email: jmagolan@uidaho.edu
,
Megha Karki
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA   Email: jmagolan@uidaho.edu
,
Jakob Magolan*
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA   Email: jmagolan@uidaho.edu
› Author Affiliations
Further Information

Publication History

Received: 24 January 2016

Accepted after revision: 22 February 2016

Publication Date:
10 March 2016 (eFirst)

Abstract

Dimethyl sulfoxide is generally characterized as a solvent and oxidant rather than as a substrate, building block, or synthon in organic chemistry. However, an abundance of reports have recently appeared that demonstrate dimethyl sulfoxide acting in these roles. This review article offers a comprehensive summary of the literature on this topic until the end of 2015. Synthetic transformations that have utilized the ‘C–S–C’, ‘C’, and ‘C–S’ fragments of dimethyl sulfoxide as building blocks are systematically summarized.

1 Introduction

2 History and Recent Highlights of DMSO-Based Oxidations

3 DMSO-Based Methylthiomethylation (–CH2SMe)

4 DMSO as a One-Carbon Synthon

4.1 DMSO-Based Methylation (–Me)

4.2 DMSO-Based Methylenation (–CH2–)

4.3 DMSO-Based Annulation/Aromatization (=CH–)

4.4 DMSO-Based Formylation (–CHO)

4.5 DMSO-Based Cyanation (–CN)

5 DMSO as Synthon for ‘S–C’ Functionalities

5.1 DMSO-Based Thiomethylation (–SMe)

5.2 DMSO-Based Methylsulfonylation (–SO2Me)

6 Summary and Conclusions

 
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