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A variety of Lewis bases were combined with 9-BBN-NTf 2 to establish the requirements for the generation of borenium cations. Five different types of behavior were found, but the most interesting was the combination of Et 3 N, DABCO, 2,6-lutidine, or Ph 3 P=S which formed borenium ions exclusively even in sub- or superstoichiometric quantities. The 9-BBN borenium ion complex of 2,6-lutidine was found to rapidly catalyze the hydrosilylation of a variety of ketones in the presence of Et 3 SiH. Preliminary mechanistic experiments suggest that the reduction involves borenium ion activation of Et 3 SiH and not the ketone.

Lewis Base Activation of Lewis Acids: Group 13. In Situ Generation and Reaction of Borenium Ions