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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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.

This article is part of the themed collection: Organic Chemistry Frontiers HOT articles for 2018

Download options Please wait...

Supplementary files

Supplementary information PDF (2356K)

Article information

DOI: https://doi.org/10.1039/C7QO01138E
Article type: Research Article
Submitted: 20 דצמ 2017
Accepted: 31 ינו 2018
First published: 01 פבר 2018

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic Chemistry Frontiers