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

• Published in: Chinese chemical letters Vol. 33; no. 2; pp. 830 - 834
• Main Authors: Gao, Peng, Ke, Miaolin, Ru, Tong, Liang, Guanfeng, Chen, Fen-Er
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier B.V 01.02.2022; Elsevier; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs,Fudan University,Shanghai 200433,China%Department of Chemistry,Sichuan University,Chengdu 610064,China; Department of Chemistry,Fudan University,Shanghai 200433,China; Department of Chemistry,Sichuan University,Chengdu 610064,China%Department of Chemistry,Fudan University,Shanghai 200433,China; Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs,Fudan University,Shanghai 200433,China
• Subjects: Aryl propionaldehydes; Chemistry; Chemistry, Multidisciplinary; Hydroformylation; Physical Sciences; Regioselectivity; Rhodium; Science & Technology; Water-soluble PNP ligands; Water-soluble PNP ligands; Aryl propionaldehydes; Regioselectivity; Rhodium; Hydroformylation; OXIDATION; ALKENES; RHODIUM(I) COMPLEXES; ALDEHYDES; REGIOSELECTIVE HYDROFORMYLATION
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2021.07.068

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-α-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. [Display omitted] 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-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio).