1,1‐Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP‐N2 Chemistry

Diphenyldiazomethane reacts with HB(C6F5)2 and B(C6F5)3, resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph2CN2BH(C6F5)2. The highly sensitive adduct Ph2CN2(B(C6F5)3) liberates N2 a...

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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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adducts
boranes
diphenyldiazomethane
Hydroboration
nitrogen
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container_end_page 16592
container_issue 52
container_start_page 16588
container_title Angewandte Chemie International Edition
container_volume 56
creator Tang, Connie
Liang, Quiming
Jupp, Andrew R.
Johnstone, Timothy C.
Neu, Rebecca C.
Song, Datong
Grimme, Stefan
Stephan, Douglas W.
description Diphenyldiazomethane reacts with HB(C6F5)2 and B(C6F5)3, resulting in 1,1‐hydroboration and adduct formation, respectively. The hydroboration proceeds via a concerted reaction involving initial formation of the Lewis adduct Ph2CN2BH(C6F5)2. The highly sensitive adduct Ph2CN2(B(C6F5)3) liberates N2 and generates Ph2CB(C6F5)3. DFT computations reveal that formation of Ph2CN2B(C6F5)3 from carbene, N2, and borane is thermodynamically favourable, suggesting steric frustration could preclude carbene–borane adduct formation and affect FLP‐N2 capture. N2 the breach… Diphenyldiazomethane reacts with HB(C6F5)2 and B(C6F5)3 to afford 1,1‐hydroboration and adduct formation, respectively. The adduct Ph2CN2B(C6F5)3 liberates N2 and the diphenylcarbene–borane adduct. Computational studies suggest that N2 capture is thermodynamically favourable, despite the exothermicity of carbene–borane adduct formation.
doi_str_mv 10.1002/anie.201710337
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subjects adducts
boranes
diphenyldiazomethane
Hydroboration
nitrogen
title 1,1‐Hydroboration and a Borane Adduct of Diphenyldiazomethane: A Potential Prelude to FLP‐N2 Chemistry
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