Trimethylsilyl triflouromethanesulfonate (TMSOTf) can act in one pot as both a silylating agent and a Lewis acid, often mediating reactivity that is difficult to achieve under other conditions.  For example, N-alkylated indoles can undergo Friedel–Crafts addition to aromatic aldehydes to yield 1:1 adducts without competing triarylmethane formation, and (trimethylsilyl)acetontitrile condenses with dimethyl acetals to yield beta-methoxy nitriles.  In addition, efficient in situ formation of silylated pi nucleophiles can lead to one-pot reactivity when residual TMSOTf catalyzes Mukaiyama-like reactivity.

Trimethylsilyl trifluoromethanesulfonate as both silylating agent and Lewis acid catalyst in organic reactions new and old

254th National Meeting (2017)

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