A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions

[Image: see text] Ni-catalyzed C–H functionalization reactions are becoming efficient routes to access a variety of functionalized arenes, yet the mechanisms of these catalytic C–C coupling reactions are not well understood. Here, we report the catalytic and stoichiometric arylation reactions of a n...

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Autores principales: Green, Kerry-Ann, Honeycutt, Aaron P., Ciccone, Sierra R., Grice, Kyle A., Baur, Andreas, Petersen, Jeffrey L., Hoover, Jessica M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167653/
https://www.ncbi.nlm.nih.gov/pubmed/37180967
http://dx.doi.org/10.1021/acscatal.2c06015
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author Green, Kerry-Ann
Honeycutt, Aaron P.
Ciccone, Sierra R.
Grice, Kyle A.
Baur, Andreas
Petersen, Jeffrey L.
Hoover, Jessica M.
author_facet Green, Kerry-Ann
Honeycutt, Aaron P.
Ciccone, Sierra R.
Grice, Kyle A.
Baur, Andreas
Petersen, Jeffrey L.
Hoover, Jessica M.
author_sort Green, Kerry-Ann
collection PubMed
description [Image: see text] Ni-catalyzed C–H functionalization reactions are becoming efficient routes to access a variety of functionalized arenes, yet the mechanisms of these catalytic C–C coupling reactions are not well understood. Here, we report the catalytic and stoichiometric arylation reactions of a nickel(II) metallacycle. Treatment of this species with silver(I)–aryl complexes results in facile arylation, consistent with a redox transmetalation step. Additionally, treatment with electrophilic coupling partners generates C–C and C–S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives.
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spelling pubmed-101676532023-05-10 A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions Green, Kerry-Ann Honeycutt, Aaron P. Ciccone, Sierra R. Grice, Kyle A. Baur, Andreas Petersen, Jeffrey L. Hoover, Jessica M. ACS Catal [Image: see text] Ni-catalyzed C–H functionalization reactions are becoming efficient routes to access a variety of functionalized arenes, yet the mechanisms of these catalytic C–C coupling reactions are not well understood. Here, we report the catalytic and stoichiometric arylation reactions of a nickel(II) metallacycle. Treatment of this species with silver(I)–aryl complexes results in facile arylation, consistent with a redox transmetalation step. Additionally, treatment with electrophilic coupling partners generates C–C and C–S bonds. We anticipate that this redox transmetalation step may be relevant to other coupling reactions that employ silver salts as additives. American Chemical Society 2023-04-24 /pmc/articles/PMC10167653/ /pubmed/37180967 http://dx.doi.org/10.1021/acscatal.2c06015 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Green, Kerry-Ann
Honeycutt, Aaron P.
Ciccone, Sierra R.
Grice, Kyle A.
Baur, Andreas
Petersen, Jeffrey L.
Hoover, Jessica M.
A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions
title A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions
title_full A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions
title_fullStr A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions
title_full_unstemmed A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions
title_short A Redox Transmetalation Step in Nickel-Catalyzed C–C Coupling Reactions
title_sort redox transmetalation step in nickel-catalyzed c–c coupling reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167653/
https://www.ncbi.nlm.nih.gov/pubmed/37180967
http://dx.doi.org/10.1021/acscatal.2c06015
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