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.
Highlights
The exploration of environmentally friendly and highly effective synthetic methods has been a significant goal of research [1-5]
Rhodium salts coordinated with proper ligands have been reported to be able to realize the activation of carbon monoxide (CO) and H2 and might achieve the reductive carbonylation of aryl iodides to afford aromatic aldehydes [37-40]
The initial reaction conditions were set as PhI (1 mmol), Rh species
Summary
The exploration of environmentally friendly and highly effective synthetic methods has been a significant goal of research [1-5]. Carbonylation processes are important transformations in the refinement and reprocessing of readily available industrial raw materials into more functionalized products. These processes generally utilize carbon monoxide (CO), currently the. In spite of its comprehensive utilization in industry, reactions involving CO are relatively seldom employed in fine chemicals syntheses. This could be due to the general difficulty of using gases as raw materials and the requirement of high-pressure equipment. Considering the efficiency and generality, this catalytic system is expected to powerfully influence both laboratory research and chemical industry by offering a practical synthetic tool for the conversion of aryl iodides to arylaldehydes
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