期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 43, 页码 23117-23122出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107856
关键词
2-arylpropanoic acids; carbon monoxide; enantioselectivity; synthetic methods; carbonylations
资金
- National Natural Science Foundation of China [NSFC-21971204, 21622203]
- Innovation Capability Support Program of Shaanxi Province [2020TD-022]
- Fund of Education Department of Shaanxi Provincial Government [21JP121]
The study presented a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation method for the synthesis of carboxylic acids, allowing for a wide range of functional group tolerance and providing a facile and atom-economical approach to 2-arylpropanoic acids.
Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.
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