Copper(II) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides

Mei-Hua Shen; Xiao-Long Lu; Hua-Dong Xu

doi:10.1039/C5RA20729K

Copper(II) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides

Mei-Hua Shen,*^a Xiao-Long Lu^a and Hua-Dong Xu*^a

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* Corresponding authors

^a School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou, China
E-mail: shenmh@cczu.edu.cn, hdxu@cczu.edu.cn

Abstract

A copper(II) acetate catalyzed ring-opening cross-coupling of cyclopropanol with sulfonyl azide has been developed. By this method, various β-amino ketones have been made efficiently in medium to high yields and venerable functional groups such as benzylic C–H, alkyl and aryl bromides, alkyl sulfonate, silyl ether and alkene are compatible with these reaction conditions. Control experiments have precluded the involvement of both radical and simple copper nitrene intermediates and a possible mechanism featuring key steps of ring-opening metalation and alkyl group migratory insertion into copper nitrene has been proposed.

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Publication details

The article was received on 19 Oct 2015, accepted on 05 Nov 2015 and first published on 09 Nov 2015

Article type: Communication

DOI: 10.1039/C5RA20729K

Author version available: Download Author version (PDF)

Citation: RSC Adv., 2015,5, 98757-98761

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Copper(II) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides

M. Shen, X. Lu and H. Xu, RSC Adv., 2015, 5, 98757
DOI: 10.1039/C5RA20729K
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Copper(II) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides

Abstract

Supplementary files

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Copper(II) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides

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