Tetrahedron Letters

Trialkylsilyl triflimides as easily tunable organocatalysts for allylation and benzylation of silyl carbon nucleophiles with non-genotoxic reagents

O Mendoza, G Rossey, L Ghosez

Index: Mendoza, Oscar; Rossey, Guy; Ghosez, Leon Tetrahedron Letters, 2010 , vol. 51, # 19 p. 2571 - 2575

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Citation Number: 5

Abstract

Trialkylsilyl triflimides generated in situ are unique catalysts for the electrophilic benzylation or allylation of trialkylsilylenol ethers or allyl trialkylsilanes with non-genotoxic alkylating reagents such as benzyl and allyl acetates. In most cases the reactions are fast at room temperature and yields are high. The reaction works particularly well with electron-rich benzyl donors including derivatives of pyrrole, indole and furane.