镍/光氧化还原催化的不对称三组分交叉偶联反应合成对映体富集的1,1-二芳基（杂芳基）烷烃。
Nickel/Photoredox-Catalyzed Asymmetric Three-Component Cross-Coupling To Access Enantioenriched 1,1-Diaryl(heteroaryl)alkanes.
作者信息
Gao Xueying, Lin Tingzhi, Wang Yan-En, Xing Fei, Qiu Yanfeng, Xiong Dan, Mao Jianyou
机构信息
School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China.
College of Science, Hebei Agricultural University, Baoding 071000, P. R. China.
出版信息
Org Lett. 2024 Oct 18;26(41):8792-8797. doi: 10.1021/acs.orglett.4c03151. Epub 2024 Oct 8.
An enantioselective 1,2-dicarbofunctionalization of vinyl (hetero)arenes with alkyl bromides and aryl bromides through nickel/photoredox catalysis is described. This three-component enantioselective domino alkyl arylation of vinyl (hetero)arenes could generate a diverse array of enantioenriched 1,1-diaryl(heteroaryl)alkanes with good to excellent yields (up to 88%) and high enantioselectivities (up to 99% ). This transformation could proceed well under mild conditions with excellent chemo- and regioselectivity due to the avoidance of the use of air- and moisture-sensitive organometallic reagents and stoichiometric metal reductants. Mechanistic studies suggested that the alkyl radical is generated via Ni species or photocatalyst.
本文描述了一种通过镍/光氧化还原催化实现乙烯基（杂）芳烃与烷基溴和芳基溴的对映选择性1,2-二碳官能化反应。这种乙烯基（杂）芳烃的三组分对映选择性多米诺烷基芳基化反应能够生成一系列对映体富集的1,1-二芳基（杂芳基）烷烃，产率良好至优异（高达88%），对映选择性高（高达99%）。由于避免使用对空气和湿气敏感的有机金属试剂和化学计量的金属还原剂，该转化反应在温和条件下能够顺利进行，具有出色的化学和区域选择性。机理研究表明，烷基自由基是通过镍物种或光催化剂生成的。
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