Applications of Lawesson’s Reagent in Organic and Organometallic Syntheses

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