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

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.

Automated summary

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.