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1,1‐Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP‐N<sub>2</sub> Chemistry

DOI

111

Citations

50

References

2017

Year

Connie Tang, Andrew R. Jupp, Timothy C. Johnstone, R.C. Neu, Datong Song, Stefan Grimme, Douglas W. Stephan
Angewandte Chemie International Edition

Abstract

Diphenyldiazomethane reacts with HB(C<sub>6</sub> F<sub>5</sub> )<sub>2</sub> and B(C<sub>6</sub> F<sub>5</sub> )<sub>3</sub> , resulting in 1,1-hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph<sub>2</sub> CN<sub>2</sub> BH(C<sub>6</sub> F<sub>5</sub> )<sub>2</sub> . The highly sensitive adduct Ph<sub>2</sub> CN<sub>2</sub> (B(C<sub>6</sub> F<sub>5</sub> )<sub>3</sub> ) liberates N<sub>2</sub> and generates Ph<sub>2</sub> CB(C<sub>6</sub> F<sub>5</sub> )<sub>3</sub> . DFT computations reveal that formation of Ph<sub>2</sub> CN<sub>2</sub> B(C<sub>6</sub> F<sub>5</sub> )<sub>3</sub> from carbene, N<sub>2</sub> , and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene-borane adduct formation and affect FLP-N<sub>2</sub> capture.

References

YearCitations

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