Citation: Peng Gao, Miaolin Ke, Tong Ru, Guanfeng Liang, Fen-Er Chen. Synthesis of rac-α-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst[J]. Chinese Chemical Letters, ;2022, 33(2): 830-834. doi: 10.1016/j.cclet.2021.07.068 shu

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

Peng Gao ^a ,
Miaolin Ke ^{b, c} ,
Tong Ru ^{b, c} ,
Guanfeng Liang ^{b, c, *} ,
Fen-Er Chen ^{a, b, c, *}

a.
Department of Chemistry, Sichuan University, Chengdu 610064, China
b.
Department of Chemistry, Fudan University, Shanghai 200433, China
c.
Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Fudan University, Shanghai 200433, China

lianggfeng@fudan.edu.cn

rfchen@fudan.edu.cn

Received Date: 27 May 2021
Revised Date: 16 July 2021
Accepted Date: 30 July 2021
Available Online: 5 August 2021

Figures(5)

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.
- Aryl propionaldehydes,
- Hydroformylation,
- Water-soluble PNP ligands,
- Regioselectivity,
- Rhodium
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