Lewis base activation of Lewis acids: Group 13. in situ generation and reaction of borenium ions

Scott E. Denmark; Yusuke Ueki

doi:10.1021/om400582k

Lewis base activation of Lewis acids: Group 13. in situ generation and reaction of borenium ions

Scott E. Denmark, Yusuke Ueki

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A variety of Lewis bases were combined with 9-BBN-NTf₂ to establish the requirements for the generation of borenium cations. Five different types of behaviors were found, but the most interesting was the combination of Et₃N, DABCO, 2,6-lutidine, or Ph₃P=S, which formed borenium ions exclusively even in sub- or superstoichiometric quantities. The 9-BBN borenium ion complex of 2,6-lutidine rapidly catalyzes the hydrosilylation of a variety of ketones in the presence of Et₃SiH. Preliminary mechanistic experiments suggest that the reduction involves borenium ion activation of Et₃SiH and not the ketone.

Original language	English (US)
Pages (from-to)	6631-6634
Number of pages	4
Journal	Organometallics
Volume	32
Issue number	22
DOIs	https://doi.org/10.1021/om400582k
State	Published - Nov 25 2013

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/om400582k

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abstract = "A variety of Lewis bases were combined with 9-BBN-NTf2 to establish the requirements for the generation of borenium cations. Five different types of behaviors were found, but the most interesting was the combination of Et3N, DABCO, 2,6-lutidine, or Ph3P=S, which formed borenium ions exclusively even in sub- or superstoichiometric quantities. The 9-BBN borenium ion complex of 2,6-lutidine rapidly catalyzes the hydrosilylation of a variety of ketones in the presence of Et3SiH. Preliminary mechanistic experiments suggest that the reduction involves borenium ion activation of Et3SiH and not the ketone.",

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AB - A variety of Lewis bases were combined with 9-BBN-NTf2 to establish the requirements for the generation of borenium cations. Five different types of behaviors were found, but the most interesting was the combination of Et3N, DABCO, 2,6-lutidine, or Ph3P=S, which formed borenium ions exclusively even in sub- or superstoichiometric quantities. The 9-BBN borenium ion complex of 2,6-lutidine rapidly catalyzes the hydrosilylation of a variety of ketones in the presence of Et3SiH. Preliminary mechanistic experiments suggest that the reduction involves borenium ion activation of Et3SiH and not the ketone.

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Lewis base activation of Lewis acids: Group 13. in situ generation and reaction of borenium ions

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