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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
ACS Central Science ( IF 12.7 ) Pub Date : 2022-07-11 , DOI: 10.1021/acscentsci.2c00204
Dong-Kai Wang 1 , Liu-Bin Li 1 , Fa-Liang Liu 1 , Hui Qiu 1 , Jiao-Zhe Li 1 , Jianfeng Zhang 1 , Chao Deng 2 , Wen-Ting Wei 1
Affiliation  

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.

中文翻译:

Fe 催化重氮化合物选择性形式插入炔丙醇的 C(sp)–C(sp3) 键:获得炔烃取代的全碳季铵中心

全碳四元中心的构建,尤其是那些含有炔取代骨架的中心,是有机合成中的一个重要挑战。在这里,我们提出了一种在温和条件下将重氮化合物选择性形式插入炔丙醇的 C(sp)-C(sp 3 ) 键的新型 Fe 催化选择性形式插入,从而能够简化构建炔烃取代的全碳四元中心。这种独特的策略首先是在羧酸存在下原位生成酯基,然后将金属-卡宾插入 C(sp)-C(sp 3 ) 键中,这可能为探索金属开辟新的反应模式-卡宾插入无环 C-C 键。
更新日期:2022-07-11
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