In(OTf) sub(3)/acid co-catalyzed hydration of 1-haloalkynes to alpha -halomethyl ketones

A novel and efficient In(OTf) sub(3) and HOAc cooperatively catalyzed hydration of 1-haloalkynes is described. This method provides ready access to alpha -chloromethyl ketones, alpha -bromomethyl ketones and alpha -iodomethyl ketones in moderate to high yields from simple, inexpensive starting mater...

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Bibliographic Details
Published in:Tetrahedron 2016-07, Vol.72 (27-28), p.3818-3822
Main Authors: Zenga, Ming, Huanga, Rui-Xue, Lib, Wen-Yi, Liub, Xiao-Wen, Heb, Fu-Ling, Zhanga, Yi-Yuan, Xiaoa, Fang
Format: Article
Language:English
Subjects:
Compatibility
Functional groups
Halides
Hydration
Ketones
Substrates
Tetrahedrons
Online Access:Get full text
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Summary:A novel and efficient In(OTf) sub(3) and HOAc cooperatively catalyzed hydration of 1-haloalkynes is described. This method provides ready access to alpha -chloromethyl ketones, alpha -bromomethyl ketones and alpha -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.
ISSN:0040-4020
DOI:10.1016/j.tet.2016.04.049