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Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)-C(sp³) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers.

ABSTRACT: 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(sp³) 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(sp³) bonds, which may open up a new reaction mode for exploring metal-carbene insertion into acyclic C-C bonds.

SUBMITTER: Wang DK

PROVIDER: S-EPMC9336152 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Fe-Catalyzed Selective Formal Insertion of Diazo Compounds into C(sp)-C(sp3) Bonds of Propargyl Alcohols: Access to Alkyne-Substituted All-Carbon Quaternary Centers.

Wang Dong-Kai DK Li Liu-Bin LB Liu Fa-Liang FL Qiu Hui H Li Jiao-Zhe JZ Zhang Jianfeng J Deng Chao C Wei Wen-Ting WT

ACS central science 20220711 7

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(sp3) 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 th ...[more]

PMID: 35912339

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