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Gold Sulfonium Benzylide Complexes Undergo Efficient Benzylidene Transfer to Alkenes

Robert G Carden, Ross A Widenhoefer

Chemistry. 2019 Aug 22;25(47):11026-11030.

PMID: 31237039

Abstract:

The gold sulfonium benzylide complexes [(P1)AuCHPh(SR1 R2 )]+ {B[3,5-CF3 C6 H3 ]4 }- [P1=P(tBu)2 o-biphenyl; R1 , R2 =-(CH2 )4 - (1 a); R1 =Et, R2 =Ph (1 b); R1 =R2 =Ph (1 c)] were synthesized by reaction of the gold α-chloro benzyl complex (P1)AuCHClPh with sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate and excess sulfide. Complexes 1 undergo efficient benzylidene transfer to alkenes and DMSO under mild conditions without external activation. Kinetic analysis of the reaction of 1 c with styrene was consistent with the intermediacy of the cationic gold benzylidene complex [(P1)AuCHPh]+ (I).

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP79060881 Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 79060-88-1 Price
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