Metal-free C(sp3)–H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization

Nan-Nan Wang; Wen-Juan Hao; Tian-Shu Zhang; Guigen Li; Ya-Nan Wu; Shu-Jiang Tu; Bo Jiang

doi:10.1039/C6CC00816J

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Metal-free C(sp³)–H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization†

Nan-Nan Wang,^a Wen-Juan Hao,^a Tian-Shu Zhang,^a Guigen Li,*^bc Ya-Nan Wu,^a Shu-Jiang Tu*^a and Bo Jiang*^ab

Author affiliations

* Corresponding authors

^a School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China
E-mail: laotu@jsnu.edu.cn, jiangchem@jsnu.edu.cn
Fax: +86 51683500065
Tel: +86 51683500065

^b Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA
E-mail: guigen.li@ttu.edu

^c Institute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University, Nanjing 210093, P. R. China

Abstract

A novel three-component carbo-oxygenation of α-diazo carbonyls for flexible synthesis of unprecedented α-aminooxy-β-amino ketones has been established through metal-free C(sp³)–H functionalization from readily accessible N,N-dimethylanilines and N-hydroxyphthalimide. The reaction pathway involves an in situ-generated phthalimide N-oxyl radical-triggered dediazotization/radical coupling sequence, leading to C–O and C–C bond formation.

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Article information

DOI: https://doi.org/10.1039/C6CC00816J
Article type: Communication
Submitted: 27 Jan 2016
Accepted: 14 Mar 2016
First published: 14 Mar 2016

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Chem. Commun., 2016,52, 5144-5147

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Metal-free C(sp³)–H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization

N. Wang, W. Hao, T. Zhang, G. Li, Y. Wu, S. Tu and B. Jiang, Chem. Commun., 2016, 52, 5144 DOI: 10.1039/C6CC00816J

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Chemical Communications