para-Selective copper-catalyzed C(sp2)–H amidation/dimerization of anilides via a radical pathway

Amol B. Viveki; Dnyaneshwar N. Garad; Rajesh G. Gonnade; Santosh B. Mhaske

doi:10.1039/C9CC09824K

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

para-Selective copper-catalyzed C(sp²)–H amidation/dimerization of anilides via a radical pathway†

Amol B. Viveki,

^ab Dnyaneshwar N. Garad,

^ab Rajesh G. Gonnade

^bc and Santosh B. Mhaske

*^ab

Author affiliations

* Corresponding authors

^a Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India
E-mail: sb.mhaske@ncl.res.in

^b Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Pune 411008, India

^c Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

Abstract

Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp²)–H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C–N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C9CC09824K
Article type: Communication
Submitted: 18 Dec 2019
Accepted: 02 Jan 2020
First published: 02 Jan 2020

Download Citation

Chem. Commun., 2020,56, 1565-1568

Permissions

Request permissions

para-Selective copper-catalyzed C(sp²)–H amidation/dimerization of anilides via a radical pathway

A. B. Viveki, D. N. Garad, R. G. Gonnade and S. B. Mhaske, Chem. Commun., 2020, 56, 1565 DOI: 10.1039/C9CC09824K

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.

Chemical Communications