4.7 Article

Electrophilic activation of difunctional aminoboranes: B-N coupling versus intramolecular Cl/Me exchange

Journal

CHEMICAL COMMUNICATIONS
Volume 58, Issue 28, Pages 4464-4467

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc00976e

Keywords

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Funding

  1. German Research Foundation (DFG) [HE 6171/4-1, HE 6171/9-1 (468457264)]
  2. Fonds der Chemischen Industrie (FCI)

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In this study, the treatment of N-silyl-B-chloro-aminoborane was investigated. It was found that substoichiometric quantities of Me3SiOTf led to B-N coupling, whereas activation with 5 mol% of Ag[Al{OC(CF3)(3)}(4)] resulted in Cl/Me exchange between the boron and the silicon center. Combined experimental and computational studies supported a chain reaction initiated by nucleation-limited chloride abstraction in the latter process.
Treatment of an N-silyl-B-chloro-aminoborane with substoichio-metric quantities of Me3SiOTf afforded B-N coupling, whereas activation with 5 mol% of Ag[Al{OC(CF3)(3)}(4)] led to Cl/Me exchange between the boron and the silicon center. Combined experimental and computational studies of the latter process support a chain reaction that is initiated by nucleation-limited chloride abstraction.

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