Litcius/Paper detail

NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes with Anthranils

Yushan Cui, Yang Gao, Wanxuan Zhao, Yinglin Luo, Haiyi Xie, Yanping Huo, Xiao‐Qiang Hu

2022The Journal of Organic Chemistry22 citationsDOI

Abstract

The regioselective hydroamination of unactivated alkenes is a long-standing challenge in organic synthesis. Herein, we report a NiH-catalyzed proximal-selective hydroamination of unactivated alkenes with 8-aminoquinoline (AQ) as a bidentate auxiliary and anthranils as aminating reagents. A wide range of primary aryl amines bearing an ortho-carbonyl group were installed in both terminal and internal unactivated alkenes, delivering a variety of valuable β- and γ-amino acid building blocks, respectively, with excellent regiocontrol. The utility of this transformation was further demonstrated by the conversion of the multifunctionalized aryl amines into useful N-heterocycles.

Topics & Concepts

HydroaminationChemistryRegioselectivityArylReagentCatalysisCombinatorial chemistryDenticityOrganic chemistryAlkylCrystal structureCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis