Organoactinide-mediated hydrothiolation of terminal alkynes with aliphatic, aromatic, and benzylic thiols

CJ Weiss, SD Wobser, TJ Marks

Index: Seo, SungYong; Yu, Xianghua; Marks, Tobin J. Journal of the American Chemical Society, 2009 , vol. 131, p. 263 - 276

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Citation Number: 83

Abstract

Atom-efficient organoactinide-catalyzed intermolecular hydrothiolation of terminal alkynes is achieved by Th (IV) and U (IV) complexes to yield vinyl sulfides. The conversion is highly Markovnikov selective and is capable of utilizing aromatic, benzylic, and aliphatic thiols. Kinetic measurements of the transformation mediated by Me2SiCp2′′ Th [CH2 (TMS)] 2 (1a; Cp′′= η5-Me4C5) shows the reaction is zero-order in [thiol], first-order in [1a], first- ...