Issue 77, 2016
From the journal:

Chemical Communications

Anti-Markovnikov rearrangement in sulfur mediated allylic C–H amination of olefins†

Zhong Zhang,a   Hongguang Du,*a   Jiaxi Xu*a  and  Pingfan Li*a  

* Corresponding authors

a State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China
E-mail: dhg@mail.buct.edu.cn, jxxu@mail.buct.edu.cn, lipf@mail.buct.edu.cn

Abstract

Cationic rearrangement reactions usually follow Markovnikov's rule to give more substituted carbocations as stable intermediates. During our study on sulfur mediated allylic C–H amination of olefins, very rare cases of anti-Markovnikov rearrangement from secondary carbocations toward primary carbocations or primary triflates were observed.

Graphical abstract: Anti-Markovnikov rearrangement in sulfur mediated allylic C–H amination of olefins

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Article information

DOI
https://doi.org/10.1039/C6CC05128F
Article type
Communication
Submitted
20 Jun 2016
Accepted
25 Aug 2016
First published
05 Sep 2016

Chem. Commun., 2016,52, 11547-11550

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Anti-Markovnikov rearrangement in sulfur mediated allylic C–H amination of olefins

Z. Zhang, H. Du, J. Xu and P. Li, Chem. Commun., 2016, 52, 11547 DOI: 10.1039/C6CC05128F

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