Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Unactivated Alkenes with α-Pyridyl Alkyl Electrophiles
Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Unactivated Alkenes with α-Pyridyl Alkyl Electrophiles
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DOI：
10.1021/acscatal.3c04147
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发表时间：
2023-11
期刊：
影响因子：
12.9
通讯作者：
Yiting Hao;Xinlin Wang;Yumeng Wu;Liangliang Song;Kui Zhang;Lingchao Cai
中科院分区：
文献类型：
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作者：
Yiting Hao;Xinlin Wang;Yumeng Wu;Liangliang Song;Kui Zhang;Lingchao Cai
具有吡啶基取代的立体中心的手性有机化合物的合成方法对于农用化学品、制药和合成实验室在其寻找独特实体中具有极大的兴趣。本文建立了一种以α-吡啶基溴代烷为催化剂，镍/Box催化剂催化烯烃对映异构聚合加氢烷基化引入立体异构C（sp3）中心的简便、模块化方法。温和的反应条件使一个显着的广泛的底物范围和良好的官能团耐受性，导致形成各种对映体富集的烷基化吡啶衍生物，以良好的产率和高对映体选择性。对映体富集的吡啶衍生物的进一步应用通过不对称的Si-H键插入来证明，利用这种模块化策略的生产效用。
Methods for the synthesis of chiral organic compounds bearing pyridyl-substituted stereogenic centers are of great interest to agrochemical, pharmaceutical, and synthetic laboratories in their search for unique entities. Here, a concise and modular method for the enantioconvergent hydroalkylation of widely available alkenes to introduce stereogenic C(sp3) centers has been establishedviaa nickel/Box catalyst with α-pyridyl alkyl bromide. The mild reaction conditions enable a remarkably broad substrate scope and good functional-group tolerance, leading to the formation of a variety of enantioenriched alkylated pyridine derivatives in good yields with high enantioselectivities. Further application of enantioenriched pyridine derivatives is demonstrated by an asymmetric Si–H bond insertion, leveraging the productive utility of this modular strategy.