Issue 87, 2018
From the journal:

Chemical Communications

Oxidative three-component 1,2-alkylarylation of alkenes with alkyl nitriles and N-heteroarenes†

Xuan-Hui Ouyang,a   Ming Hu,a   Ren-Jie Song*a  and  Jin-Heng Li ORCID logo *abc  

* Corresponding authors

a Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
E-mail: srj0731@hnu.edu.cn, jhli@hnu.edu.cn

b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

c Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Hunan Normal University), Ministry of Education, Changsha, Hunan 410081, China

Abstract

An indium-promoted intermolecular oxidative 1,2-alkylarylation of alkenes with alkyl nitriles and N-heteroarenes enabled by C(sp3)–H/C(sp2)–H functionalization is presented. This oxidative radical strategy allows the formation of two new C–C bonds through transformations of two different C–H bonds across the alkenes in a controlled single-step manner, and offers a general, highly atom-economic route for the production of new functionalized N-heteroarenes, including indoles, pyrrolo[2,3-b]pyridine, pyrrolo[3,2,1-ij]quinolone and pyrroles.

Graphical abstract: Oxidative three-component 1,2-alkylarylation of alkenes with alkyl nitriles and N-heteroarenes

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Article information

DOI
https://doi.org/10.1039/C8CC06509H
Article type
Communication
Submitted
09 Aug 2018
Accepted
08 Oct 2018
First published
08 Oct 2018

Chem. Commun., 2018,54, 12345-12348

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Oxidative three-component 1,2-alkylarylation of alkenes with alkyl nitriles and N-heteroarenes

X. Ouyang, M. Hu, R. Song and J. Li, Chem. Commun., 2018, 54, 12345 DOI: 10.1039/C8CC06509H

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