Copper-catalyzed C–H [3 + 2] annulation of N-substituted anilines with α-carbonyl alkyl bromides via C(sp3)–Br/C(sp2)–H functionalization?

Organic & Biomolecular Chemistry Pub Date: 2020-03-02 DOI: 10.1039/D0OB00399A

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.

Graphical abstract: Copper-catalyzed C–H [3 + 2] annulation of N-substituted anilines with α-carbonyl alkyl bromides via C(sp3)–Br/C(sp2)–H functionalization
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