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Synthesis 2003(13): 1929-1958  
DOI: 10.1055/s-2003-41447
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Applications of Lawesson’s Reagent in Organic and Organometallic Syntheses

Martin Jesberger*, Thomas P. Davis, Leonie Barner
Centre for Advanced Macromolecular Design, School of Chemical Engineering and Industrial Chemistry, The University of New South Wales, Sydney NSW 2052, Australia
Fax: +61(2)93856250; e-Mail: camd@unsw.edu.au;
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Publikationsverlauf

Received 24 March 2003
Publikationsdatum:
10. September 2003 (online)

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Abstract

This review, including 245 references, describes the application of Lawesson’s reagent [2,4-bis(p-methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulfide] LR in organic and organometallic syntheses. Thionations of carbonyl-containing compounds as well as unexpected reactions are shown for different applications (e.g. cyclizations, rerrangements, syntheses of heterocyclic compounds etc.). Syntheses of novel organometallic compounds by LR are also discussed.

1 Introduction

2 Mechanism of the Thionation Reaction Using Lawesson’s Reagent

3 Reactions with Carbonyl-Containing Compounds

3.1 Ketones

3.2 Esters and Lactones

3.3 Amides and Lactams

3.4 Amino Acids, Peptides, Nucleosides, and Nucleotides

3.5 Macrocycles and Polymers

4 Cyclization Reactions to Thiophenes, Thiazoles and Other Compounds

5 Synthesis of Heteroatom-Containing Compounds

5.1 Sulfur-Containing Heterocyclic Compounds

5.2 Phosphorus- and Sulfur-Containing Heterocycles

5.3 Other Phosphorus- and Sulfur-Containing Compounds

6 Synthesis of Organometallic Compounds

6.1 Transition Metals

6.2 Main Group Metals

7 Usage of Lawesson’s Reagent for Special Syntheses

7.1 Glycosidations

7.2 Transformation of Alcohols to Thiols

7.3 Reduction of Sulfoxides

7.4 Catalyst for Aldol Reactions

7.5 Preparation of Other Compounds

8 Unexpected Reactions Following the Usage of Lawesson’s Reagent

9 References

Key words

Lawesson’s reagent - thionation - organothiophos­phorus reagent - heterocycles - sulfur-compounds - organometallic compounds