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Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas.


ABSTRACT: The reductive carbonylation of aryl iodides to aryl aldehydes possesses broad application prospects. We present an efficient and facile Rh-based catalytic system composed of the commercially available Rh salt RhCl3·3H2O, PPh3 as phosphine ligand, and Et3N as the base, for the synthesis of arylaldehydes via the reductive carbonylation of aryl iodides with CO and H2 under relatively mild conditions with a broad substrate range affording the products in good to excellent yields. Systematic investigations were carried out to study the experimental parameters. We explored the optimal ratio of Rh salt and PPh3 ligand, substrate scope, carbonyl source and hydrogen source, and the reaction mechanism. Particularly, a scaled-up experiment indicated that the catalytic method could find valuable applications in industrial productions. The low gas pressure, cheap ligand and low metal dosage could significantly improve the practicability in both chemical researches and industrial applications.

SUBMITTER: Liu Z 

PROVIDER: S-EPMC7155901 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas.

Liu Zhenghui Z   Wang Peng P   Yan Zhenzhong Z   Chen Suqing S   Yu Dongkun D   Zhao Xinhui X   Mu Tiancheng T  

Beilstein journal of organic chemistry 20200408


The reductive carbonylation of aryl iodides to aryl aldehydes possesses broad application prospects. We present an efficient and facile Rh-based catalytic system composed of the commercially available Rh salt RhCl<sub>3</sub>·3H<sub>2</sub>O, PPh<sub>3</sub> as phosphine ligand, and Et<sub>3</sub>N as the base, for the synthesis of arylaldehydes via the reductive carbonylation of aryl iodides with CO and H<sub>2</sub> under relatively mild conditions with a broad substrate range affording the pr  ...[more]

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