Sequential carboxylation/intramolecular cyclization reaction of o-alkynyl acetophenone with CO2

Wen-Zhen Zhang; Ling-Long Shi; Chuang Liu; Xu-Tong Yang; Yan-Bo Wang; Yi Luo; Xiao-Bing Lu

doi:10.1039/C3QO00047H

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

Sequential carboxylation/intramolecular cyclization reaction of o-alkynyl acetophenone with CO₂†

Wen-Zhen Zhang,*^a Ling-Long Shi,^a Chuang Liu,^a Xu-Tong Yang,^a Yan-Bo Wang,^a Yi Luo^a and Xiao-Bing Lu*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, P. R. China
E-mail: zhangwz@dlut.edu.cn, lxb-1999@163.com
Fax: +86 411 8498 6256
Tel: +86 411 8498 6257

Abstract

A novel sequential carboxylation/intramolecular cyclization reaction of o-alkynyl acetophenone with CO₂ was developed for producing the synthetically important 1(3H)-isobenzofuranylidene acetic acids and esters in good yield and exclusive selectivity toward 5-exo oxygen cyclization under very mild reaction conditions (room temperature and CO₂ balloon). This efficient reaction system showed wide functional group compatibility. Also, the computational study successfully explained the exclusive product selectivity toward the 5-exo oxygen cyclization product.

Download options Please wait...

Supplementary files

Article information

DOI: https://doi.org/10.1039/C3QO00047H
Article type: Research Article
Submitted: 21 Nov 2013
Accepted: 27 Jan 2014
First published: 03 Mar 2014

Download Citation

Org. Chem. Front., 2014,1, 275-283

Permissions

Request permissions

Sequential carboxylation/intramolecular cyclization reaction of o-alkynyl acetophenone with CO₂

W. Zhang, L. Shi, C. Liu, X. Yang, Y. Wang, Y. Luo and X. Lu, Org. Chem. Front., 2014, 1, 275 DOI: 10.1039/C3QO00047H

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.

Organic Chemistry Frontiers