Synthesis of Carbonyl-Containing Oxindoles via Ni-Catalyzed Reductive Aryl-Acylation and Aryl-Esterification of Alkenes

Abstract

Carbonyl-containing oxindoles are ubiquitous core structures present in many biologically active natural products and pharmaceutical molecules. Nickel-catalyzed reductive aryl-acylation of alkenes using aryl anhydrides or alkanoyl chlorides as acyl sources is developed, providing 3,3-disubstituted oxindoles bearing ketone functionality at the 3-position. Moreover, nickel-catalyzed reductive aryl-esterification of alkenes using chloroformate as ester sources is further developed, affording 3,3-disubstituted oxindoles bearing ester functionality at the 3-position. This strategy has the advantages of good yields and high functional group compatibility.

Keywords

• nickel catalysis
• reductive coupling reaction
• aryl-acylation
• aryl-esterification
• oxindoles