通过有机光催化下自由基介导的与硅烷的远程1,4-迁移实现未活化烯烃的硅基化和（杂）芳基/烯基化反应。
Silylation and (Hetero)aryl/alkenylation of Unactivated Alkenes via Radical-Mediated Distal 1,4-Migration with Hydrosilanes under Organophotocatalysis.
作者信息
Wang Ting, Chen Lu, Liu Yuan-Yuan, Zhang Zheng-Bing, Han Pan, Jing Lin-Hai
机构信息
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong, Sichuan 637002, People's Republic of China.
出版信息
Org Lett. 2024 May 31;26(21):4526-4531. doi: 10.1021/acs.orglett.4c01414. Epub 2024 May 18.
We report a novel organic photoredox catalysis to achieve unprecedented γ-(hetero)aryl/alkenyl-δ-silyl aliphatic amines via silyl-mediated distal (hetero)aryl/alkenyl migration of aromatic/alkenyl amines bearing unactivated alkenes with hydrosilanes. This protocol features mild and metal-free reaction conditions, high atom economy, excellent selectivity, and functional group compatibility. Mechanistic studies suggest that silylation and (hetero)aryl/alkenylation involve photoredox hydrogen atom transfer catalysis and subsequent 1,4-migration of a remote (hetero)aryl/alkenyl group from nitrogen to carbon.
我们报道了一种新型有机光氧化还原催化方法，该方法通过硅烷介导的带有未活化烯烃的芳香族/烯基胺的（杂）芳基/烯基迁移与硅氢化物反应，实现了前所未有的γ-（杂）芳基/烯基-δ-硅烷基脂肪胺的合成。该方法具有温和且无金属的反应条件、高原子经济性、优异的选择性和官能团兼容性。机理研究表明，硅烷化和（杂）芳基/烯基化涉及光氧化还原氢原子转移催化以及随后远程（杂）芳基/烯基从氮到碳的1,4-迁移。
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