Synthesis of rac-α-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-alpha-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

This work presents the preparation and synthetic application of a class of water-soluble PNP ligands. These ligands were incorporated into catalysts and successfully used for the regioselective hydroformylation of arylalkenes, providing efficient access to α-aryl propionaldehydes with high yield and selectivity. The synthetic methodology was further demonstrated through gram-scale synthesis and diverse transformations for non-steroidal antiinflammatory drugs.