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Copper-Catalyzed Si-B Bond Activation in the Nucleophilic Substitution of Primary Aliphatic Triflates

Jonas Scharfbier, Martin Oestreich*

*Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 115, 10623 Berlin, Germany, Email:

J. Scharfbier, M. Oestreich, Synlett, 2016, 27, 1274-1276.

DOI: 10.1055/s-0035-1561407


In a nucleophilic displacement of the triflate leaving group attached to terminally functionalized alkyl groups, copper catalysis is used to release the silicon nucleophile from Suginome's Si-B reagent. The functional group tolerance is excellent, the reaction even tolerates halide leaving groups.

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Key Words

chemoselectivity, copper, nucleophilic substitution, silicon, transmetalation, alkylsilanes

ID: J60-Y2016