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Synthesis 2008(16): 2491-2509  
DOI: 10.1055/s-2008-1067188
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

Recent Developments in Disulfide Bond Formation

Dariusz Witt*
Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-952 Gdansk, Poland
Fax: +48(58)3472694; e-Mail: dwitt@chem.pg.gda.pl;
Further Information

Publication History

Received 12 March 2008
Publication Date:
24 July 2008 (online)

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Abstract

This review summarizes the recent developments of di­sulfide bond formation with a variety of reagents. The scope and limitations of the presented methods are discussed. The syntheses of unsymmetrical disulfides are highlighted in order to present the most versatile achievements.

1 Introduction

2 Preparation of Disulfides

2.1 By Oxidation of Thiols

2.2 By Reductive Coupling of Sulfonyl Chlorides

2.3 By Reaction with Sulfur Monochloride

2.4 By Radical Cyclization of Substituted Aminothiourea Derivatives­

2.5 Using 1-Chlorobenzotriazole

2.6 From Elemental Sulfur

2.7 From Organophosphorus Sulfenyl Bromide

2.8 From N-Trifluoroacetyl Arenesulfenamides

2.9 Using Phase-Transfer Catalysis

2.10 From a Thiol-Disulfide Exchange Reaction

2.11 From Thiocyanates

2.12 From 2-(Trimethylsilyl)ethyl Sulfides

2.13 From Thiosulfonates and Thiosulfates

2.14 From Thioesters

2.15 By Disulfide Exchange Reactions

2.16 From Tetrathiomolybdate

2.17 By Miscellaneous Reactions

3 Conclusions

Key words

disulfides - thiols - synthesis - symmetrical disulfides - unsymmetrical disulfides