Stereoselective Synthesis of Z Fluoroalkenes through Copper‐Catalyzed Hydrodefluorination of gem‐Difluoroalkenes with Water. Issue 43 (22nd September 2017)

• Record Type: Journal Article
• Authors: Hu, Jiefeng; Han, Xiaowei; Yuan, Yu; Shi, Zhuangzhi
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 43(2017)
• Page Start: 13342
• Page End: 13346
• Publication Date: 2017-09-22
• Subjects: copper -- fluorine -- fluoroalkanes -- hydrodefluorination -- Z selectivity; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201708224
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A copper catalytic system was established for the stereoselective hydrodefluorination of gem‐difluoroalkenes through C−F activation to synthesize various Z fluoroalkenes. H2 O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good‐functional group compatibility, accepting a range of carbonyls as precursors to the gem‐difluoroalkenes, including aliphatic, aromatic, and α, β‐unsaturated aldehydes and even ketones. It serves as a powerful synthetic method for the late‐stage modification of complex compounds. Abstract : From A(ll) to Z : A copper catalytic system was established for the stereoselective hydrodefluorination of carbonyl‐derived gem ‐difluoroalkenes with water through C−F activation. This route employs readily available aldehydes or ketones, cheap fluorine and hydrogen sources, and an earth‐abundant metal as the catalyst, and it can be employed to construct Z fluoroalkenes without considering the Z / E configuration of the substrates or intermediates.