Ruthenium-catalyzed Umpolung Carboxylation of Hydrazones with CO

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 Jun 19

PMID 29910940

Citations 7

Authors

Si-Shun Yan

Lei Zhu

Jian-Heng Ye

Zhen Zhang

He Huang

Huiying Zeng

Chao-Jun Li

Yu Lan

Da-Gang Yu

Affiliations

Soon will be listed here.

Abstract

The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO 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 CO.

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