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Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles

The development of Cu-catalyzed addition of carbon nucleophiles to vinylidene cyclopropanes was reported. The reactions with 1,1-bisborylmethane provided homopropargylic boronate products by forming a C–C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes. Alkynyl boro...

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Autores principales: Chen, Jichao, Gao, Shang, Chen, Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7020789/
https://www.ncbi.nlm.nih.gov/pubmed/32110346
http://dx.doi.org/10.1039/c9sc04122b
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author Chen, Jichao
Gao, Shang
Chen, Ming
author_facet Chen, Jichao
Gao, Shang
Chen, Ming
author_sort Chen, Jichao
collection PubMed
description The development of Cu-catalyzed addition of carbon nucleophiles to vinylidene cyclopropanes was reported. The reactions with 1,1-bisborylmethane provided homopropargylic boronate products by forming a C–C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes. Alkynyl boronates are also suitable nucleophile precursors in reactions with vinylidene cyclopropanes, and skipped diynes were obtained in high yields. In addition, the Cu-enolate generated from the initial addition of nucleophilic copper species to vinylidene cyclopropanes can be intercepted by an external electrophile. As such, vinylidene cyclopropane serves as a linchpin to connect a nucleophile and an electrophile by forming two carbon–carbon bonds sequentially.
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spelling pubmed-70207892020-02-27 Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles Chen, Jichao Gao, Shang Chen, Ming Chem Sci Chemistry The development of Cu-catalyzed addition of carbon nucleophiles to vinylidene cyclopropanes was reported. The reactions with 1,1-bisborylmethane provided homopropargylic boronate products by forming a C–C bond at the terminal carbon atom of the allene moiety of vinylidene cyclopropanes. Alkynyl boronates are also suitable nucleophile precursors in reactions with vinylidene cyclopropanes, and skipped diynes were obtained in high yields. In addition, the Cu-enolate generated from the initial addition of nucleophilic copper species to vinylidene cyclopropanes can be intercepted by an external electrophile. As such, vinylidene cyclopropane serves as a linchpin to connect a nucleophile and an electrophile by forming two carbon–carbon bonds sequentially. Royal Society of Chemistry 2019-10-09 /pmc/articles/PMC7020789/ /pubmed/32110346 http://dx.doi.org/10.1039/c9sc04122b Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Chen, Jichao
Gao, Shang
Chen, Ming
Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles
title Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles
title_full Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles
title_fullStr Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles
title_full_unstemmed Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles
title_short Cu-catalyzed C–C bond formation of vinylidene cyclopropanes with carbon nucleophiles
title_sort cu-catalyzed c–c bond formation of vinylidene cyclopropanes with carbon nucleophiles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7020789/
https://www.ncbi.nlm.nih.gov/pubmed/32110346
http://dx.doi.org/10.1039/c9sc04122b
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AT gaoshang cucatalyzedccbondformationofvinylidenecyclopropaneswithcarbonnucleophiles
AT chenming cucatalyzedccbondformationofvinylidenecyclopropaneswithcarbonnucleophiles