1,1-Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP-N 2 Chemistry

Diphenyldiazomethane reacts with HB(C F ) and B(C F ) , resulting in 1,1-hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph CN BH(C F ) . The highly sensitive adduct Ph CN (B(C F ) ) liberates N and...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-12, Vol.56 (52), p.16588-16592
Main Authors: Tang, Connie, Liang, Quiming, Jupp, Andrew R, Johnstone, Timothy C, Neu, Rebecca C, Song, Datong, Grimme, Stefan, Stephan, Douglas W
Format: Article
Language:English
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Summary:Diphenyldiazomethane reacts with HB(C F ) and B(C F ) , resulting in 1,1-hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph CN BH(C F ) . The highly sensitive adduct Ph CN (B(C F ) ) liberates N and generates Ph CB(C F ) . DFT computations reveal that formation of Ph CN B(C F ) from carbene, N , and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene-borane adduct formation and affect FLP-N capture.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201710337