ChemInform Abstract: Synthesis of 1,1‐Disubstituted Alkyl Vinyl Sulfides via Rhodium‐Catalyzed Alkyne Hydrothiolation: Scope and Limitations.

Abstract

Thioethers P 0430Synthesis of 1,1-Disubstituted Alkyl Vinyl Sulfides via Rhodium-Catalyzed Alkyne Hydrothiolation: Scope and Limitations. -The Rh catalyst (RHB) efficiently promotes the addition of thiols to various alkynes. Reaction of terminal alkynes generally proceeds with excellent regioselectivity yielding the branched adducts. The propiolate (VI), however, gives the linear isomers. Some functional groups such as halides, nitriles, amines, and esters are tolerated but strongly coordinating ones like 2-pyridine and carboxylic acids prevent the addition. -(YANG, J.; SABARRE, A.; FRASER, L. R.; PATRICK, B. O.; LOVE*, J. A.; J. Org. Chem. 74 (2009) 1, 182-187; Dep. Chem., Univ. British Columbia, Vancouver, B. C. V6T 1Z1, Can.; Eng.) -Jannicke 18-056