Gold Sulfonium Benzylide Complexes Undergo Efficient Benzylidene Transfer to Alkenes.

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).

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Author Ross A. Widenhoefer Chemistry