Issue 82, 2019

Direct bromocarboxylation of arynes using allyl bromides and carbon dioxide

Abstract

An unprecedented three-component coupling involving arynes, allyl bromides, and CO2 is described, providing efficient and facile access to structurally diverse ortho-brominated aryl esters. Unlike the conventional role played in organic synthesis as electrophiles, organic bromides served as nucleophiles in this reaction, affording a new approach to multicomponent reactions (MCRs) involving aryne intermediates. Additionally, Hammett analysis suggests that two reaction mechanisms exist, depending on the electronic nature of the cinnamyl bromides used.

Graphical abstract: Direct bromocarboxylation of arynes using allyl bromides and carbon dioxide

Supplementary files

Article information

Article type
Communication
Submitted
28 Jūl. 2019
Accepted
18 Sept. 2019
First published
19 Sept. 2019

Chem. Commun., 2019,55, 12304-12307

Direct bromocarboxylation of arynes using allyl bromides and carbon dioxide

Y. Zhang, W. Xiong, J. Cen, W. Yan, Y. Wu, C. Qi, W. Wu and H. Jiang, Chem. Commun., 2019, 55, 12304 DOI: 10.1039/C9CC05495B

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