Nickel-catalyzed acylzincation of allenes with organozincs and CO

Transition metal-catalyzed carbonylative reaction with CO gas are among the central task in organic synthesis, enabling the construction of highly valuable carbonyl compound. Here, we show an earth-abundant nickel-catalyzed three-component tandem acylzincation/cyclization sequence of allene and alky...

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Autores principales: Wu, Xianqing, Wang, Chenglong, Liu, Ning, Qu, Jingping, Chen, Yifeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10618444/
https://www.ncbi.nlm.nih.gov/pubmed/37907542
http://dx.doi.org/10.1038/s41467-023-42716-2
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author Wu, Xianqing
Wang, Chenglong
Liu, Ning
Qu, Jingping
Chen, Yifeng
author_facet Wu, Xianqing
Wang, Chenglong
Liu, Ning
Qu, Jingping
Chen, Yifeng
author_sort Wu, Xianqing
collection PubMed
description Transition metal-catalyzed carbonylative reaction with CO gas are among the central task in organic synthesis, enabling the construction of highly valuable carbonyl compound. Here, we show an earth-abundant nickel-catalyzed three-component tandem acylzincation/cyclization sequence of allene and alkylzinc reagent with 1 atm of CO under mild conditions. This protocol is featured by broad functional group tolerance with high reaction selectivity, providing a rapid and convenient synthetic method for the construction of diverse fully substituted benzotropone derivatives. Mechanistic studies reveal that the installation of a cyano group tethered to allene moiety enables the high regio- and stereoselectivity of this acylzincation of allene, allowing the selective formation of three consecutive C-C bonds in a highly efficient manner.
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spelling pubmed-106184442023-11-02 Nickel-catalyzed acylzincation of allenes with organozincs and CO Wu, Xianqing Wang, Chenglong Liu, Ning Qu, Jingping Chen, Yifeng Nat Commun Article Transition metal-catalyzed carbonylative reaction with CO gas are among the central task in organic synthesis, enabling the construction of highly valuable carbonyl compound. Here, we show an earth-abundant nickel-catalyzed three-component tandem acylzincation/cyclization sequence of allene and alkylzinc reagent with 1 atm of CO under mild conditions. This protocol is featured by broad functional group tolerance with high reaction selectivity, providing a rapid and convenient synthetic method for the construction of diverse fully substituted benzotropone derivatives. Mechanistic studies reveal that the installation of a cyano group tethered to allene moiety enables the high regio- and stereoselectivity of this acylzincation of allene, allowing the selective formation of three consecutive C-C bonds in a highly efficient manner. Nature Publishing Group UK 2023-10-31 /pmc/articles/PMC10618444/ /pubmed/37907542 http://dx.doi.org/10.1038/s41467-023-42716-2 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Wu, Xianqing
Wang, Chenglong
Liu, Ning
Qu, Jingping
Chen, Yifeng
Nickel-catalyzed acylzincation of allenes with organozincs and CO
title Nickel-catalyzed acylzincation of allenes with organozincs and CO
title_full Nickel-catalyzed acylzincation of allenes with organozincs and CO
title_fullStr Nickel-catalyzed acylzincation of allenes with organozincs and CO
title_full_unstemmed Nickel-catalyzed acylzincation of allenes with organozincs and CO
title_short Nickel-catalyzed acylzincation of allenes with organozincs and CO
title_sort nickel-catalyzed acylzincation of allenes with organozincs and co
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10618444/
https://www.ncbi.nlm.nih.gov/pubmed/37907542
http://dx.doi.org/10.1038/s41467-023-42716-2
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