In(OTf)3/acid co-catalyzed hydration of 1-haloalkynes to α-halomethyl ketones. Issue 27 (7th July 2016)

• Record Type: Journal Article
• Authors: Zeng, Ming; Huang, Rui-Xue; Li, Wen-Yi; Liu, Xiao-Wen; He, Fu-Ling; Zhang, Yi-Yuan; Xiao, Fang
• Is Part Of: Tetrahedron. Volume 72:Issue 27/28(2016)
• Page Start: 3818
• Page End: 3822
• Publication Date: 2016-07-07
• Subjects: Hydration -- Indium -- Cooperative catalysis -- 1-Haloalkyne -- α-Halomethyl ketone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.04.049
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A novel and efficient In(OTf)3 and HOAc cooperatively catalyzed hydration of 1-haloalkynes is described. This method provides ready access to α-chloromethyl ketones, α-bromomethyl ketones and α-iodomethyl ketones in moderate to high yields from simple, inexpensive starting materials. A broad substrate scope is achieved, and the reaction is compatible with various functional groups, including alkoxy, trifluoromethyl, halide, hydroxyl, cyclohexyl, and heterocyclic groups. Graphical abstract: