Synlett

Regio-and stereoselective copper-catalyzed addition of aromatic and aliphatic thiols to terminal and internal nonactivated alkynes

IG Trostyanskaya, IP Beletskaya

Index: Trostyanskaya, Inna G.; Beletskaya, Irina P. Synlett, 2012 , # 4 p. 535 - 540

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Citation Number: 11

Abstract

The addition of thiols to terminal alkynes, catalyzed by transition metals, [¹²] lanthanides and actinides, [¹³] allows to obtain alkenyl sulfides with high regioselectivity, forming either α- (Markovnikov addition) or β-isomers (anti-Markovnikov addition). Formation of the α-isomer involves the insertion of alkyne into M-SR bond followed by the protonolysis of the CM bond (M = Pd). ... It should be pointed out that the β-isomer can be also obtained in simple base-catalyzed addition ...

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