Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation

[Image: see text] A carbonylation–carboxylation synthetic sequence, via double CO(2) fixation, is described. The productive merger of a Ni-catalyzed cross-electrophile coupling manifold, with the use of AlCl(3), triggered a cascade reaction with the formation of three consecutive C–C bonds in a sing...

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Autores principales: Giovanelli, Riccardo, Lombardi, Lorenzo, Pedrazzani, Riccardo, Monari, Magda, Reis, Marta Castiñeira, López, Carlos Silva, Bertuzzi, Giulio, Bandini, Marco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10546374/
https://www.ncbi.nlm.nih.gov/pubmed/37669466
http://dx.doi.org/10.1021/acs.orglett.3c02394
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author Giovanelli, Riccardo
Lombardi, Lorenzo
Pedrazzani, Riccardo
Monari, Magda
Reis, Marta Castiñeira
López, Carlos Silva
Bertuzzi, Giulio
Bandini, Marco
author_facet Giovanelli, Riccardo
Lombardi, Lorenzo
Pedrazzani, Riccardo
Monari, Magda
Reis, Marta Castiñeira
López, Carlos Silva
Bertuzzi, Giulio
Bandini, Marco
author_sort Giovanelli, Riccardo
collection PubMed
description [Image: see text] A carbonylation–carboxylation synthetic sequence, via double CO(2) fixation, is described. The productive merger of a Ni-catalyzed cross-electrophile coupling manifold, with the use of AlCl(3), triggered a cascade reaction with the formation of three consecutive C–C bonds in a single operation. This strategy traces an unprecedented synthetic route to ketones under Lewis acid assisted carbon dioxide valorization. Computational insights revealed a unique double function of AlCl(3), and labeling ((13)CO(2)) experiments validate the genuine incorporation of CO(2) in both functional groups.
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spelling pubmed-105463742023-10-04 Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation Giovanelli, Riccardo Lombardi, Lorenzo Pedrazzani, Riccardo Monari, Magda Reis, Marta Castiñeira López, Carlos Silva Bertuzzi, Giulio Bandini, Marco Org Lett [Image: see text] A carbonylation–carboxylation synthetic sequence, via double CO(2) fixation, is described. The productive merger of a Ni-catalyzed cross-electrophile coupling manifold, with the use of AlCl(3), triggered a cascade reaction with the formation of three consecutive C–C bonds in a single operation. This strategy traces an unprecedented synthetic route to ketones under Lewis acid assisted carbon dioxide valorization. Computational insights revealed a unique double function of AlCl(3), and labeling ((13)CO(2)) experiments validate the genuine incorporation of CO(2) in both functional groups. American Chemical Society 2023-09-05 /pmc/articles/PMC10546374/ /pubmed/37669466 http://dx.doi.org/10.1021/acs.orglett.3c02394 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 Giovanelli, Riccardo
Lombardi, Lorenzo
Pedrazzani, Riccardo
Monari, Magda
Reis, Marta Castiñeira
López, Carlos Silva
Bertuzzi, Giulio
Bandini, Marco
Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation
title Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation
title_full Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation
title_fullStr Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation
title_full_unstemmed Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation
title_short Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO(2) Incorporation
title_sort nickel catalyzed carbonylation/carboxylation sequence via double co(2) incorporation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10546374/
https://www.ncbi.nlm.nih.gov/pubmed/37669466
http://dx.doi.org/10.1021/acs.orglett.3c02394
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