Copper-catalyzed tandem radical amination/1, 2-carbon migration of allylic alcohols: Direct access to α-quaternary-β-amino ketones

doi:10.1016/S1872-2067(17)62915-2

Chinese Journal of Catalysis ›› 2018, Vol. 39 ›› Issue (1): 138-145.DOI: 10.1016/S1872-2067(17)62915-2

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Copper-catalyzed tandem radical amination/1, 2-carbon migration of allylic alcohols: Direct access to α-quaternary-β-amino ketones

Jiaqiong Sun, Guangfan Zheng, Yongmei Fu, Qiao Zhang, Yimin Wang, Qian Zhang, Yan Li, Qian Zhang

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University, Changchun 130024, Jilin, China

Received:2017-09-04 Revised:2017-09-15 Online:2018-01-18 Published:2018-01-19
Contact: 10.1016/S1872-2067(17)62915-2
Supported by:
This work was supported by the National Natural Science Foundation of China (21372041), Changbai Mountain Scholarship Program, and the Fundamental Research Funds for the Central Universities (2412016KJ006).

Abstract

Abstract:

A novel nitrogen-centered radical-induced 1,2-carbon migration reaction of allylic alcohols has been developed. This method provides easy access to a variety of α-quaternary-β-amino ketones under mild reaction conditions. The reaction has a wide substrate scope and operational simplicity. Mechanistic studies suggest that 1,2-carbon migration is induced by regioselective nitrogen-centered radical addition to the alkene unit.

Key words: Allylic alcohols, Nitrogen-centered radicals, 1,2-Carbon migration, α-Quaternary-β-amino ketones, N-F regent

Jiaqiong Sun, Guangfan Zheng, Yongmei Fu, Qiao Zhang, Yimin Wang, Qian Zhang, Yan Li, Qian Zhang. Copper-catalyzed tandem radical amination/1, 2-carbon migration of allylic alcohols: Direct access to α-quaternary-β-amino ketones[J]. Chinese Journal of Catalysis, 2018, 39(1): 138-145.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(17)62915-2

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Copper-catalyzed tandem radical amination/1, 2-carbon migration of allylic alcohols: Direct access to α-quaternary-β-amino ketones

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