Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers

[Image: see text] The construction of all-carbon quaternary centers, especially those containing an alkyne-substituted framework, represents an important challenge in organic synthesis. Here we present a novel Fe-catalyzed selective formal insertion of diazo compounds into C(sp)–C(sp(3)) bonds of pr...

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Autores principales: Wang, Dong-Kai, Li, Liu-Bin, Liu, Fa-Liang, Qiu, Hui, Li, Jiao-Zhe, Zhang, Jianfeng, Deng, Chao, Wei, Wen-Ting
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9336152/
https://www.ncbi.nlm.nih.gov/pubmed/35912339
http://dx.doi.org/10.1021/acscentsci.2c00204
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author Wang, Dong-Kai
Li, Liu-Bin
Liu, Fa-Liang
Qiu, Hui
Li, Jiao-Zhe
Zhang, Jianfeng
Deng, Chao
Wei, Wen-Ting
author_facet Wang, Dong-Kai
Li, Liu-Bin
Liu, Fa-Liang
Qiu, Hui
Li, Jiao-Zhe
Zhang, Jianfeng
Deng, Chao
Wei, Wen-Ting
author_sort Wang, Dong-Kai
collection PubMed
description [Image: see text] The construction of all-carbon quaternary centers, especially those containing an alkyne-substituted framework, represents an important challenge in organic synthesis. Here we present a novel Fe-catalyzed selective formal insertion of diazo compounds into C(sp)–C(sp(3)) bonds of propargyl alcohols under mild conditions that enables the streamlined construction of alkyne-substituted all-carbon quaternary centers. This unique strategy starts with in situ generation of an ester group in the presence of carboxylic acids, followed by insertion of metal-carbene into C(sp)–C(sp(3)) bonds, which may open up a new reaction mode for exploring metal-carbene insertion into acyclic C–C bonds.
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spelling pubmed-93361522022-07-30 Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers Wang, Dong-Kai Li, Liu-Bin Liu, Fa-Liang Qiu, Hui Li, Jiao-Zhe Zhang, Jianfeng Deng, Chao Wei, Wen-Ting ACS Cent Sci [Image: see text] The construction of all-carbon quaternary centers, especially those containing an alkyne-substituted framework, represents an important challenge in organic synthesis. Here we present a novel Fe-catalyzed selective formal insertion of diazo compounds into C(sp)–C(sp(3)) bonds of propargyl alcohols under mild conditions that enables the streamlined construction of alkyne-substituted all-carbon quaternary centers. This unique strategy starts with in situ generation of an ester group in the presence of carboxylic acids, followed by insertion of metal-carbene into C(sp)–C(sp(3)) bonds, which may open up a new reaction mode for exploring metal-carbene insertion into acyclic C–C bonds. American Chemical Society 2022-07-11 2022-07-27 /pmc/articles/PMC9336152/ /pubmed/35912339 http://dx.doi.org/10.1021/acscentsci.2c00204 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Wang, Dong-Kai
Li, Liu-Bin
Liu, Fa-Liang
Qiu, Hui
Li, Jiao-Zhe
Zhang, Jianfeng
Deng, Chao
Wei, Wen-Ting
Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers
title Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers
title_full Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers
title_fullStr Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers
title_full_unstemmed Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers
title_short Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)–C(sp(3)) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers
title_sort fe-catalyzed selective formal insertion of diazo compounds into c(sp)–c(sp(3)) bonds of propargyl alcohols: access to alkyne-substituted all-carbon quaternary centers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9336152/
https://www.ncbi.nlm.nih.gov/pubmed/35912339
http://dx.doi.org/10.1021/acscentsci.2c00204
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