Microwave-Assisted Copper-Catalyzed Oxidative Cyclization of Acrylamides with Non-Activated Ketones

Yaping Zhao; Nandini Sharma; Upendra K Sharma; Zhenghua Li; Gonghua Song; Erik V Van der Eycken

doi:10.1002/chem.201504776

Microwave-Assisted Copper-Catalyzed Oxidative Cyclization of Acrylamides with Non-Activated Ketones

Chemistry. 2016 Apr 18;22(17):5878-82. doi: 10.1002/chem.201504776. Epub 2016 Mar 10.

Authors

Yaping Zhao^{1

2}, Nandini Sharma³, Upendra K Sharma¹, Zhenghua Li¹, Gonghua Song², Erik V Van der Eycken⁴

Affiliations

¹ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, Belgium.
² Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, Shanghai, 200237, People's Republic of China.
³ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, Belgium. n_sharma023@yahoo.co.in.
⁴ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001, Leuven, Belgium. erik.vandereycken@chem.kuleuven.be.

PMID: 26868308
DOI: 10.1002/chem.201504776

Abstract

An operationally simple and efficient microwave-assisted protocol for the oxidative cyclization of acrylamide derivatives with non-activated ketones to generate 3,3-disubstituted oxindoles is described. The reaction proceeds by a copper-catalyzed tandem radical addition/cyclization strategy and tolerates a series of functional groups with moderate to excellent yields.

Keywords: alkenes; copper; ketones; oxindoles; radical addition.

Publication types

Research Support, Non-U.S. Gov't