Issue 10, 2014
From the journal:

Organic & Biomolecular Chemistry

Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction†

Jun Qiuab  and  Ronghua Zhang*ab  

* Corresponding authors

a Department of Chemistry, Tongji University, Shanghai 200092, P. R. China

b Key Laboratory of Yangtze River Water Environment, Ministry of Education, Siping Road 1239, Shanghai, P. R. China
E-mail: rhzhang@tongji.edu.cn

Abstract

A novel and metal-free acrylamides formation between arylpropynes and hydroxylamine hydrochloride through sp3 C–H and C–C bond cleavage has been achieved with DDQ as an oxidant. The mechanistic study shows that the acrylamides are formed through a three-step tandem sequence, including cross-dehydrogenative-coupling (CDC) reaction, aza-Meyer–Schuster rearrangement and Beckmann rearrangement.

Graphical abstract: Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction

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Article information

DOI
https://doi.org/10.1039/C3OB42444H
Article type
Communication
Submitted
06 Dec 2013
Accepted
28 Jan 2014
First published
28 Jan 2014

Org. Biomol. Chem., 2014,12, 1556-1560

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Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction

J. Qiu and R. Zhang, Org. Biomol. Chem., 2014, 12, 1556 DOI: 10.1039/C3OB42444H

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