A Highly Regioselective Cyanothiolation of Alkynes via Oxidative Addition of Thiocyanates to Tetrakis(triphenylphosphine)palladium(0) Catalyst

Abstract

Tetrakis(triphenylphosphine)palladium(0) catalyzes the highly regioselective addition of phenyl thiocyanate (PhSCN) to terminal alkynes, which attains the simultaneous introduction of thio and cyano groups to the internal and terminal positions of alkynes, respectively. This reaction may proceed via the oxidative addition of PhSCN to Pd(PPh 3 ) 4, which forms Pd(SPh)(CN)(PPh 3 ) 2 as the key intermediate.