Copper-catalyzed ring-opening C(sp3)–N coupling of cycloketone oxime esters: access to 1°, 2° and 3° alkyl amines

Li Tian; Shuangqiu Gao; Rui Wang; Yang Li; Chunlin Tang; Lili Shi; Junkai Fu

doi:10.1039/C9CC02030F

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Copper-catalyzed ring-opening C(sp³)–N coupling of cycloketone oxime esters: access to 1°, 2° and 3° alkyl amines†

Li Tian,^a Shuangqiu Gao,^a Rui Wang,^a Yang Li,^a Chunlin Tang,^a Lili Shi*^b and Junkai Fu

*^ab

Author affiliations

* Corresponding authors

^a Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China
E-mail: fujk109@nenu.edu.cn

^b Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China
E-mail: shill@pkusz.edu.cn

Abstract

A novel copper-catalyzed C(sp³)–N coupling of cycloketone oxime esters with nitrogen nucleophiles has been realized. All of the N-aryl/alkylanilines, anilines and benzophenone imine could be employed in this protocol to produce a variety of 1°, 2° and 3° alkyl amines in one or two steps. These resultant cyano-containing alkyl amines were proven to be versatile synthetic building blocks in a variety of chemical transformations.

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Article information

DOI: https://doi.org/10.1039/C9CC02030F
Article type: Communication
Submitted: 13 Mar 2019
Accepted: 08 Apr 2019
First published: 09 Apr 2019

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Chem. Commun., 2019,55, 5347-5350

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Copper-catalyzed ring-opening C(sp³)–N coupling of cycloketone oxime esters: access to 1°, 2° and 3° alkyl amines

L. Tian, S. Gao, R. Wang, Y. Li, C. Tang, L. Shi and J. Fu, Chem. Commun., 2019, 55, 5347 DOI: 10.1039/C9CC02030F

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