Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds

The reactions of FLPs with diazomethanes leads to the rapid loss of N(2). In contrast, in this work, we reported reactions of phosphine/borane FLPs with chlorodiazirines which led to the reduction of the N=N double bond, affording linked phosphinimide/amidoborate zwitterions of the general form R(3)...

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Autores principales: Mandal, Dipendu, Chen, Ting, Qu, Zheng‐Wang, Grimme, Stefan, Stephan, Douglas W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9543150/
https://www.ncbi.nlm.nih.gov/pubmed/35830598
http://dx.doi.org/10.1002/anie.202209241
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author Mandal, Dipendu
Chen, Ting
Qu, Zheng‐Wang
Grimme, Stefan
Stephan, Douglas W.
author_facet Mandal, Dipendu
Chen, Ting
Qu, Zheng‐Wang
Grimme, Stefan
Stephan, Douglas W.
author_sort Mandal, Dipendu
collection PubMed
description The reactions of FLPs with diazomethanes leads to the rapid loss of N(2). In contrast, in this work, we reported reactions of phosphine/borane FLPs with chlorodiazirines which led to the reduction of the N=N double bond, affording linked phosphinimide/amidoborate zwitterions of the general form R(3)PNC(Ar)NR′BX(C(6)F(5))(2). A detailed DFT mechanistic study showed that these reactions proceed via FLP addition to the N=N bond, followed by subsequent group transfer reactions to nitrogen and capture of the halide anion.
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spelling pubmed-95431502022-10-14 Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds Mandal, Dipendu Chen, Ting Qu, Zheng‐Wang Grimme, Stefan Stephan, Douglas W. Angew Chem Int Ed Engl Communications The reactions of FLPs with diazomethanes leads to the rapid loss of N(2). In contrast, in this work, we reported reactions of phosphine/borane FLPs with chlorodiazirines which led to the reduction of the N=N double bond, affording linked phosphinimide/amidoborate zwitterions of the general form R(3)PNC(Ar)NR′BX(C(6)F(5))(2). A detailed DFT mechanistic study showed that these reactions proceed via FLP addition to the N=N bond, followed by subsequent group transfer reactions to nitrogen and capture of the halide anion. John Wiley and Sons Inc. 2022-08-03 2022-09-12 /pmc/articles/PMC9543150/ /pubmed/35830598 http://dx.doi.org/10.1002/anie.202209241 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Mandal, Dipendu
Chen, Ting
Qu, Zheng‐Wang
Grimme, Stefan
Stephan, Douglas W.
Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds
title Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds
title_full Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds
title_fullStr Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds
title_full_unstemmed Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds
title_short Reactions of Frustrated Lewis Pairs with Chloro‐Diazirines: Cleavage of N=N Double Bonds
title_sort reactions of frustrated lewis pairs with chloro‐diazirines: cleavage of n=n double bonds
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9543150/
https://www.ncbi.nlm.nih.gov/pubmed/35830598
http://dx.doi.org/10.1002/anie.202209241
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