Cu-Catalyzed Multicomponent Reaction of Styrenes, Perfluoroalkyl Halide, Alcohol, and tert-Butyl Hydroperoxide: One-Pot Synthesis of (Z)-β-Alkoxyperfluoroalkenone

Qiang Luo; Chunmei Liu; Jingjing Tong; Ying Shao; Wenyu Shan; Hanghang Wang; Hao Zheng; Jiang Cheng; Xiaobing Wan

doi:10.1021/acs.joc.5b02664

Cu-Catalyzed Multicomponent Reaction of Styrenes, Perfluoroalkyl Halide, Alcohol, and tert-Butyl Hydroperoxide: One-Pot Synthesis of (Z)-β-Alkoxyperfluoroalkenone

J Org Chem. 2016 Apr 15;81(8):3103-11. doi: 10.1021/acs.joc.5b02664. Epub 2016 Mar 25.

Authors

Qiang Luo¹, Chunmei Liu¹, Jingjing Tong², Ying Shao², Wenyu Shan¹, Hanghang Wang¹, Hao Zheng², Jiang Cheng², Xiaobing Wan¹

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University , Suzhou 215123, P. R. China.
² Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University , Changzhou, 213164, P. R. China.

PMID: 26980724
DOI: 10.1021/acs.joc.5b02664

Abstract

An efficient synthesis of Z-perfluoroalkyl-substituted enones by a multicomponent reaction strategy has been described. A variety of elusive perfluoroalkylated enones are furnished under mild reaction conditions in good yields with unique chemo- and stereoselectivity. A sequence of radical-mediated Kornblum-DeLaMare reaction, Michael addition, and HF elimination is proposed for the mechanism.

Publication types

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