A nickel-mediated oxidative α-C(sp3)–H functionalization of amides with allylic alcohols terminated by radical 1,2-aryl migration

Ren-Jie Song; Yong-Qiang Tu; Dao-Yong Zhu; Fu-Min Zhang; Shao-Hua Wang

doi:10.1039/C4CC08797F

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A nickel-mediated oxidative α-C(sp³)–H functionalization of amides with allylic alcohols terminated by radical 1,2-aryl migration†

Ren-Jie Song,^ab Yong-Qiang Tu,*^ac Dao-Yong Zhu,^a Fu-Min Zhang^a and Shao-Hua Wang^a

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* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
E-mail: tuyq@lzu.edu.cn

^b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China

^c Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300000, P. R. China

Abstract

A Ni-mediated oxidative C(sp³)–H functionalization of N,N-substituted amides with α,α-diaryl allylic alcohols through a radical 1,2-aryl migration process has been developed. This process features a broad substrate scope and excellent functional group tolerance. Notably, γ-amino ketones containing an all-carbon quaternary center were synthesized under these conditions in moderate to good yields.

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Article information

DOI: https://doi.org/10.1039/C4CC08797F
Article type: Communication
Submitted: 04 Nov 2014
Accepted: 11 Nov 2014
First published: 18 Nov 2014

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Chem. Commun., 2015,51, 749-752

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A nickel-mediated oxidative α-C(sp³)–H functionalization of amides with allylic alcohols terminated by radical 1,2-aryl migration

R. Song, Y. Tu, D. Zhu, F. Zhang and S. Wang, Chem. Commun., 2015, 51, 749 DOI: 10.1039/C4CC08797F

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