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

Tang, Connie ; Liang, Quiming ; Jupp, Andrew R ; Johnstone, Timothy C ; Neu, Rebecca C ; Song, Datong ; Grimme, Stefan ; Stephan, Douglas W

Angewandte Chemie International Edition, 2017-12, Vol.56 (52), p.16588-16592 [Periódico revisado por pares]

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Título:
1,1-Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP-N 2 Chemistry
Autor: Tang, Connie ; Liang, Quiming ; Jupp, Andrew R ; Johnstone, Timothy C ; Neu, Rebecca C ; Song, Datong ; Grimme, Stefan ; Stephan, Douglas W
É parte de: Angewandte Chemie International Edition, 2017-12, Vol.56 (52), p.16588-16592
Descrição: 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.
Editor: Germany
Idioma: Inglês

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