转鼓
电泳剂
烯烃
芳基
催化作用
酒
试剂
化学
基质(水族馆)
镍
烯丙基重排
酯交换
有机化学
组合化学
药物化学
烷基
亲核细胞
生物
生态学
作者
Taeho Kang,Nana Kim,Peter T. Cheng,Hao Zhang,Klement Foo,Keary M. Engle
标识
DOI:10.26434/chemrxiv.14195426.v1
摘要
An alcohol-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents is reported. This transformation is enabled by specifically tailored O -(2,6-dimethoxybenzoyl)hydroxylamine electrophiles that suppress competitive processes, including undesired β-hydride elimination and transesterification between the alcohol substrate and electrophile. The reaction delivers the desired 1,2-carboaminated products with excellent regio- and diastereoselectivity and exhibits a broad scope of coupling partners and alkenes, including complex natural products. Various mechanistic experiments and analysis of the stereochemical outcome with a cyclic alkene substrate, as confirmed by X-ray crystallographic analysis, support alcohol-directed syn -insertion of an organonickel(I) species.
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