Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction

[Image: see text] A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been established. This method enables the synthesis of 3,5-vicinal carbocyclic rings found in numerous biologically active compounds and natural products. We provide mechanistic experiments that...

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Autores principales: Hewitt, Kirsten A., Herbert, Claire A., Jarvo, Elizabeth R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9396665/
https://www.ncbi.nlm.nih.gov/pubmed/35926218
http://dx.doi.org/10.1021/acs.orglett.2c02481
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author Hewitt, Kirsten A.
Herbert, Claire A.
Jarvo, Elizabeth R.
author_facet Hewitt, Kirsten A.
Herbert, Claire A.
Jarvo, Elizabeth R.
author_sort Hewitt, Kirsten A.
collection PubMed
description [Image: see text] A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been established. This method enables the synthesis of 3,5-vicinal carbocyclic rings found in numerous biologically active compounds and natural products. We provide mechanistic experiments that indicate this reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds through radical intermediates.
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spelling pubmed-93966652022-08-24 Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction Hewitt, Kirsten A. Herbert, Claire A. Jarvo, Elizabeth R. Org Lett [Image: see text] A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been established. This method enables the synthesis of 3,5-vicinal carbocyclic rings found in numerous biologically active compounds and natural products. We provide mechanistic experiments that indicate this reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds through radical intermediates. American Chemical Society 2022-08-04 2022-08-19 /pmc/articles/PMC9396665/ /pubmed/35926218 http://dx.doi.org/10.1021/acs.orglett.2c02481 Text en © 2022 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 Hewitt, Kirsten A.
Herbert, Claire A.
Jarvo, Elizabeth R.
Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction
title Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction
title_full Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction
title_fullStr Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction
title_full_unstemmed Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction
title_short Synthesis of Vicinal Carbocycles by Intramolecular Nickel-Catalyzed Conjunctive Cross-Electrophile Coupling Reaction
title_sort synthesis of vicinal carbocycles by intramolecular nickel-catalyzed conjunctive cross-electrophile coupling reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9396665/
https://www.ncbi.nlm.nih.gov/pubmed/35926218
http://dx.doi.org/10.1021/acs.orglett.2c02481
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