Issue 22, 2020

Experimental and theoretical study on the cyclic(alkyl)(amino)carbene-copper catalyzed Friedel–Crafts reaction of N,N-dialkylanilines with styrenes

Abstract

The Friedel–Crafts reaction of alkalinous substrates is challenging because of the coordination between amines and traditional acid catalysts. Based on theoretical research, we designed a catalytic process for the Friedel–Crafts reactions of N,N-dialkylanilines in the presence of CAAC-CuCl [CAAC = cyclic(alkyl)(amino)carbene] and KB(C6F5)4. Experimental results show that the catalytic system is suitable for a series of N,N-dialkylanilines and styrenes with good to excellent yields of para-selectivity products. The results are comparable to those obtained in carbene-gold catalyzed processes.

Graphical abstract: Experimental and theoretical study on the cyclic(alkyl)(amino)carbene-copper catalyzed Friedel–Crafts reaction of N,N-dialkylanilines with styrenes

Supplementary files

Article information

Article type
Paper
Submitted
24 Dec 2019
Accepted
18 May 2020
First published
18 May 2020

Org. Biomol. Chem., 2020,18, 4272-4275

Experimental and theoretical study on the cyclic(alkyl)(amino)carbene-copper catalyzed Friedel–Crafts reaction of N,N-dialkylanilines with styrenes

W. Ma, G. Zhai, X. Hu and Y. Wu, Org. Biomol. Chem., 2020, 18, 4272 DOI: 10.1039/C9OB02734C

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements