Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations

While (Ph(2)CN(2))B(C(6)F(5))(3) is unstable, single electron transfer from Cp*(2)Co affords the isolation of stable products [Cp*(2)Co][Ph(2)CNNHB(C(6)F(5))(3)] 1 and [Cp*Co(C(5)Me(4)CH(2)B(C(6)F(5))(3))] 2. The analogous combination of Ph(2)CN(2) and BPh(3) showed no evidence of adduct formation a...

Descripción completa

Detalles Bibliográficos
Autores principales: Cao, Levy L., Zhou, Jiliang, Qu, Zheng‐Wang, Stephan, Douglas W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972512/
https://www.ncbi.nlm.nih.gov/pubmed/31589360
http://dx.doi.org/10.1002/anie.201912338
_version_ 1783489847780966400
author Cao, Levy L.
Zhou, Jiliang
Qu, Zheng‐Wang
Stephan, Douglas W.
author_facet Cao, Levy L.
Zhou, Jiliang
Qu, Zheng‐Wang
Stephan, Douglas W.
author_sort Cao, Levy L.
collection PubMed
description While (Ph(2)CN(2))B(C(6)F(5))(3) is unstable, single electron transfer from Cp*(2)Co affords the isolation of stable products [Cp*(2)Co][Ph(2)CNNHB(C(6)F(5))(3)] 1 and [Cp*Co(C(5)Me(4)CH(2)B(C(6)F(5))(3))] 2. The analogous combination of Ph(2)CN(2) and BPh(3) showed no evidence of adduct formation and yet single electron transfer from Cp*(2)Cr affords the species [Cp*(2)Cr][PhC(C(6)H(4))NNBPh(3)] 3 and [Cp*(2)Cr][Ph(2)CNNHBPh(3)] 4. Computations showed both reactions proceed via transient radical anions of the diphenyldiazomethane–borane adducts to effect C−H bond activations.
format Online
Article
Text
id pubmed-6972512
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-69725122020-01-27 Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations Cao, Levy L. Zhou, Jiliang Qu, Zheng‐Wang Stephan, Douglas W. Angew Chem Int Ed Engl Communications While (Ph(2)CN(2))B(C(6)F(5))(3) is unstable, single electron transfer from Cp*(2)Co affords the isolation of stable products [Cp*(2)Co][Ph(2)CNNHB(C(6)F(5))(3)] 1 and [Cp*Co(C(5)Me(4)CH(2)B(C(6)F(5))(3))] 2. The analogous combination of Ph(2)CN(2) and BPh(3) showed no evidence of adduct formation and yet single electron transfer from Cp*(2)Cr affords the species [Cp*(2)Cr][PhC(C(6)H(4))NNBPh(3)] 3 and [Cp*(2)Cr][Ph(2)CNNHBPh(3)] 4. Computations showed both reactions proceed via transient radical anions of the diphenyldiazomethane–borane adducts to effect C−H bond activations. John Wiley and Sons Inc. 2019-10-30 2019-12-16 /pmc/articles/PMC6972512/ /pubmed/31589360 http://dx.doi.org/10.1002/anie.201912338 Text en ©2019 The Authors published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim This is an open access article under the terms of the http://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
Cao, Levy L.
Zhou, Jiliang
Qu, Zheng‐Wang
Stephan, Douglas W.
Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations
title Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations
title_full Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations
title_fullStr Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations
title_full_unstemmed Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations
title_short Single Electron Transfer to Diazomethane–Borane Adducts Prompts C−H Bond Activations
title_sort single electron transfer to diazomethane–borane adducts prompts c−h bond activations
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6972512/
https://www.ncbi.nlm.nih.gov/pubmed/31589360
http://dx.doi.org/10.1002/anie.201912338
work_keys_str_mv AT caolevyl singleelectrontransfertodiazomethaneboraneadductspromptschbondactivations
AT zhoujiliang singleelectrontransfertodiazomethaneboraneadductspromptschbondactivations
AT quzhengwang singleelectrontransfertodiazomethaneboraneadductspromptschbondactivations
AT stephandouglasw singleelectrontransfertodiazomethaneboraneadductspromptschbondactivations

Ejemplares similares