Copper-catalyzed C–H [3 + 2] annulation of <i>N</i>-substituted anilines with α-carbonyl alkyl bromides <i>via</i> C(sp<sup>3</sup>)–Br/C(sp<sup>2</sup>)–H functionalization
An-Zhu Cao, Yuting Xiao, Yan‐Chen Wu, Ren‐Jie Song, Ye‐Xiang Xie, Jin‐Heng Li
Abstract
A copper-catalyzed C-H [3 + 2] annulation of N-substituted anilines with α-carbonyl alkyl bromides for the synthesis of 3,3'-disubstituted oxindoles is developed. Tandem C-H cycloamidation reactions of various α-carbonyl alkyl bromide derivatives including tertiary-α-bromoalkyl ketone esters, malonic esters and cycloalkanes, with N-aryl or alkyl substituted anilines, can be performed using this system, affording a vast array of valuable 3,3'-disubstituted oxindoles in moderate to good yields.
Topics & Concepts
ChemistryAnnulationAlkylKetoneMedicinal chemistryCatalysisBromideArylOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms