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CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 at room temperature

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Abstract

A CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 in the presence of trimethylsilylacetylene was developed to give functionalized propiolic acid products at room temperature. A wide range of propiolic acids bearing functional groups was successfully obtained in good to excellent yields. Mechanistic studies demonstrate that in the carboxylation process the alkynylsilane intermediate was first in situ generated, which was then trapped by CO2, giving rise to the corresponding functionalized propiolic acids after acidification. The advantages of this approach include avoiding use of transition-metal catalysts, wide substrate scope together with excellent functional group tolerance, ambient conditions and a facile work-up procedure.

Graphical abstract: CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 at room temperature

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Publication details

The article was received on 22 May 2017, accepted on 17 Jul 2017 and first published on 18 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01779K
Citation: New J. Chem., 2017, Advance Article
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    CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 at room temperature

    B. Yu, P. Yang, X. Gao, Z. Z. Yang, Y. F. Zhao, H. Y. Zhang and Z. M. Liu, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01779K

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