Applications of Lawesson's reagent in organic and organometallic syntheses

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.