n        Bu4NOTf-promoted radical self-hydrogen transferring isomerization under transition metal-free conditions

Hong-Xing Zheng; Chuan-Zhi Yao; Jian-Ping Qu; Yan-Biao Kang

doi:10.1039/C7QO01138E

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ⁿBu₄NOTf-promoted radical self-hydrogen transferring isomerization under transition metal-free conditions†

Hong-Xing Zheng,‡^ab Chuan-Zhi Yao,‡^b Jian-Ping Qu

*^a and Yan-Biao Kang

*^b

Author affiliations

* Corresponding authors

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China
E-mail: ias_jpqu@njtech.edu.cn

^b Centre of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China
E-mail: ybkang@ustc.edu.cn

Abstract

We report the first allylic isomerization of alcohols catalyzed by ⁿBu₄NOTf generated in situ from tetrabutylammonium triflate and potassium tert-butoxide. Substituted ketones could be prepared under mild conditions in good to excellent yields. The relationship between catalysts and their reactivity has been investigated by systematic kinetic studies. The radical nature of this isomerization reaction has also been confirmed.

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Article information

DOI: https://doi.org/10.1039/C7QO01138E
Article type: Research Article
Submitted: 20 Dec 2017
Accepted: 31 Jan 2018
First published: 01 Feb 2018

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Org. Chem. Front., 2018,5, 1213-1216

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ⁿBu₄NOTf-promoted radical self-hydrogen transferring isomerization under transition metal-free conditions

H. Zheng, C. Yao, J. Qu and Y. Kang, Org. Chem. Front., 2018, 5, 1213 DOI: 10.1039/C7QO01138E

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