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Synlett 2018; 29(12): 1634-1638
DOI: 10.1055/s-0037-1609968
letter
© Georg Thieme Verlag Stuttgart · New York

Substrate-Controlled Regioselective Iodooxygenation of Olefins

Xiaoqing Li*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: xqli@zjut.edu.cn   Email: future@zjut.edu.cn
,
Kun Chen
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: xqli@zjut.edu.cn   Email: future@zjut.edu.cn
,
Yucai Tang
b   College of Chemistry and Material Engineering, Hunan University of Arts and Science, Changde, 415000, P. R. of China
,
Huanhuan Zhu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: xqli@zjut.edu.cn   Email: future@zjut.edu.cn
,
Feng Chen
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: xqli@zjut.edu.cn   Email: future@zjut.edu.cn
,
Xinhuan Yan
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: xqli@zjut.edu.cn   Email: future@zjut.edu.cn
,
Xiangsheng Xu*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: xqli@zjut.edu.cn   Email: future@zjut.edu.cn
› Author AffiliationsFinancial support from the National Key Research and Development Program of China (2017YFC0210900), the National Natural Science Foundation of China (21102130), the Natural Science Foundation of Zhejiang Province (LY14B020005) and Training Plan for College Students' Innovation and Entrepreneurship of ZJUT is greatly appreciated.
Further Information

Publication History

Received: 07 March 2018

Accepted after revision: 16 April 2018

Publication Date:
23 May 2018 (online)

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Abstract

An unexpected regioselective I2/TBHP-mediated 1,2-iodo­oxygenation of alkenes with N-hydroxylamines is described. The reaction proceeds through a radical coupling mechanism or a iodonium mechanism, which is controlled by the structures of both N-hydroxylamines and alkenes, to form vicinal iodo-substituted N-alkoxyamines regioselectively. Both the iodo and alkoxyamine group of the resulting products offer rich possibilities of synthetic manipulations.

Key words

iodooxygenation - regioselectivity - alkenes - N-hydroxyphthalimide - 1-hydroxybenzotriazole

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609968.
  • Supporting Information
 

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