Tianjin Key Laboratory of Structure and Performance for Functional Molecules; College of Chemistry, Tianjin Normal University, Tianjin, 300387, People's Republic of China.
Nat Commun. 2021 Nov 1;12(1):6280. doi: 10.1038/s41467-021-26527-x.
Few methods have been reported for intermolecular arylamination of alkenes, which could provide direct access to important arylethylamine scaffolds. Herein, we report an intermolecular syn-1,2-arylamination of unactivated alkenes with arylboronic acids and O-benzoylhydroxylamine electrophiles with Ni(II) catalyst. The cleavable bidentate picolinamide directing group facilitates formation of stabilized 4-, 5- or 6-membered nickelacycles and enables the difunctionalization of diverse alkenyl amines with high levels of regio-, chemo- and diastereocontrol. This general and practical protocol is compatible with broad substrate scope and high functional group tolerance. The utility of this method is further demonstrated by the site-selective modification of pharmaceutical agents.
目前报道的用于烯烃分子间芳基胺化的方法很少，这些方法可以直接得到重要的芳基乙胺骨架。在此，我们报道了镍（II）催化剂作用下，芳基硼酸和邻苯甲酰基羟胺亲电试剂与未活化烯烃的分子间 syn-1,2-芳基胺化反应。可裂解的双齿吡啶甲酰胺导向基团有利于稳定的 4-、5-或 6 元镍环的形成，并能以高区域、化学和非对映选择性对各种烯基胺进行双官能化。该通用且实用的方案与广泛的底物范围和高官能团容忍度兼容。该方法的实用性通过药物试剂的选择性修饰进一步得到证明。
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