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Issue 21, 2018
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Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2

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Abstract

The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2 to generate important aryl acetic acids is reported. Besides aldehyde hydrazones, a variety of ketone hydrazones, which have not been successfully applied in previous umpolung reactions with other reactive electrophiles, also show high reactivity and selectivity under mild conditions. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and offers easy derivation of important structures, including bioactive felbinac and adiphenine. Computational studies reveal that this umpolung reaction proceeds through the generation of a Ru-nitrenoid followed by concerted [4 + 2] cycloaddition with CO2.

Graphical abstract: Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2

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Supplementary files

Article information


Submitted
20 Mar 2018
Accepted
27 Apr 2018
First published
30 Apr 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 4873-4878
Article type
Edge Article

Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2

S. Yan, L. Zhu, J. Ye, Z. Zhang, H. Huang, H. Zeng, C. Li, Y. Lan and D. Yu, Chem. Sci., 2018, 9, 4873
DOI: 10.1039/C8SC01299G

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