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Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation
Author(s) -
Sang Rui,
Kucmierczyk Peter,
Dühren Ricarda,
Razzaq Rauf,
Dong Kaiwu,
Liu Jie,
Franke Robert,
Jackstell Ralf,
Beller Matthias
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201908451
Subject(s) - catalysis , chemistry , steric effects , organic chemistry , aqueous solution , carboxylic acid , palladium , ligand (biochemistry) , polymer , combinatorial chemistry , biochemistry , receptor
The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous‐phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra‐, tri‐, and 1,1‐disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key‐to‐success is the use of a built‐in‐base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost‐competitive processes for the industrial production of carboxylic acids.