Computational and experimental studies on copper-mediated selective cascade C-H/N-H annulation of electron-deficient acrylamide with arynes.

Affiliation

Sixth People's Hospital South Campus, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, and School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China. [Email]

Abstract

An efficient and convenient copper-mediated method has been developed to achieve direct cascade C-H/N-H annulation to synthesize 2-quinolinones from electron-deficient acrylamides and arynes. This method highlights an emerging but simple strategy to transform inert C-H bonds into versatile functional groups in organic synthesis to provide a new method of synthesizing 2-quinolinones efficiently. Mechanistic investigations by experimental and density functional theory (DFT) studies suggest that an organometallic C-H activation via a Cu(iii) intermediate is likely to be involved in the reaction.