Nickel/Photo-Cocatalyzed Regioselective Ring Opening of <i>N</i>-Tosyl Styrenyl Aziridines with Aldehydes
作者:Pei Fan、Youxiang Jin、Jiawei Liu、Rui Wang、Chuan Wang
DOI:10.1021/acs.orglett.1c02514
日期:2021.10.1
Aldehydes and aziridines are both intrinsic electrophilic reagents, and thus the coupling reaction between these two compounds is highly challenging. In this protocol, the merger of nickel and hydrogen-atom-transfer photocatalysis successfully enables the ring opening of N-tosyl styrenyl aziridines with aldehydes, providing a novel and atom-economical access to a variety of β-amino ketones with complete
醛和氮丙啶都是固有的亲电试剂,因此这两种化合物之间的偶联反应极具挑战性。在该协议中,镍和氢原子转移光催化的合并成功地使N-甲苯磺酰基苯乙烯基氮丙啶与醛开环,为获得具有完全区域控制的各种 β-氨基酮提供了一种新颖且原子经济的途径。初步机理研究表明,开环反应以协同催化模式进行:醛在辐照下被四丁基十钨酸铵转化为酰基,而镍催化剂参与氮丙啶的开环和以下碳-碳键的形成步。