Issue 35, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles†

Wei Zhou,a   Yicheng Zhang,a   Pinhua Lia  and  Lei Wang*ab  

* Corresponding authors

a Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P R China
E-mail: leiwang@chnu.edu.cn
Fax: +86-561-309-0518
Tel: +86-561-380-2069

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China

Abstract

A Na2CO3-promoted addition of phenols to propiolonitriles generated (Z)-3-aryloxy-acrylonitriles in nearly quantitative yields with exclusively Z-isomers, and a DABCO-promoted addition reaction of phenols with propiolonitriles afforded mainly (E)-3-aryloxy-acrylonitriles with high yields. The obtained (E)-3-aryloxy-acrylonitriles underwent intramolecular cyclization to give 3-cyanobenzofurans in good yields through palladium-catalyzed direct C–H bond functionalization.

Graphical abstract: Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB25969A
Article type
Paper
Submitted
19 May 2012
Accepted
03 Jul 2012
First published
05 Jul 2012

Org. Biomol. Chem., 2012,10, 7184-7196

Permissions

Request permissions

Synthesis of (Z)-3-aryloxy-acrylonitriles, (E)-3-aryloxy-acrylonitriles and 3-cyanobenzofurans through the sequential reactions of phenols with propiolonitriles

W. Zhou, Y. Zhang, P. Li and L. Wang, Org. Biomol. Chem., 2012, 10, 7184 DOI: 10.1039/C2OB25969A

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