Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation

Readily available cyclohexa‐2,5‐dien‐1‐ylcarbonyl chloride derivatives are introduced as bench‐stable HCl surrogates for transfer hydrochlorination of terminal and internal alkenes as well as selected alkynes. The stepwise Grob fragmentation of those acyl chlorides into chloride, carbon monoxide, a...

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Autores principales: Xie, Kaixue, Oestreich, Martin
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/PMC9321001/
https://www.ncbi.nlm.nih.gov/pubmed/35325506
http://dx.doi.org/10.1002/anie.202203692
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author Xie, Kaixue
Oestreich, Martin
author_facet Xie, Kaixue
Oestreich, Martin
author_sort Xie, Kaixue
collection PubMed
description Readily available cyclohexa‐2,5‐dien‐1‐ylcarbonyl chloride derivatives are introduced as bench‐stable HCl surrogates for transfer hydrochlorination of terminal and internal alkenes as well as selected alkynes. The stepwise Grob fragmentation of those acyl chlorides into chloride, carbon monoxide, a low‐molecular‐weight arene, and a proton is promoted by B(C(6)F(5))(3). This decarbonylative transfer process enables the addition of HCl across C−C double and triple bonds with Markovnikov selectivity at room temperature.
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spelling pubmed-93210012022-07-30 Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation Xie, Kaixue Oestreich, Martin Angew Chem Int Ed Engl Communications Readily available cyclohexa‐2,5‐dien‐1‐ylcarbonyl chloride derivatives are introduced as bench‐stable HCl surrogates for transfer hydrochlorination of terminal and internal alkenes as well as selected alkynes. The stepwise Grob fragmentation of those acyl chlorides into chloride, carbon monoxide, a low‐molecular‐weight arene, and a proton is promoted by B(C(6)F(5))(3). This decarbonylative transfer process enables the addition of HCl across C−C double and triple bonds with Markovnikov selectivity at room temperature. John Wiley and Sons Inc. 2022-04-11 2022-06-13 /pmc/articles/PMC9321001/ /pubmed/35325506 http://dx.doi.org/10.1002/anie.202203692 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
Xie, Kaixue
Oestreich, Martin
Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation
title Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation
title_full Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation
title_fullStr Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation
title_full_unstemmed Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation
title_short Decarbonylative Transfer Hydrochlorination of Alkenes and Alkynes Based on a B(C(6)F(5))(3)‐Initiated Grob Fragmentation
title_sort decarbonylative transfer hydrochlorination of alkenes and alkynes based on a b(c(6)f(5))(3)‐initiated grob fragmentation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9321001/
https://www.ncbi.nlm.nih.gov/pubmed/35325506
http://dx.doi.org/10.1002/anie.202203692
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