2270-20-4Relevant articles and documents
Homoenolic radical derived from propionic acid: A versatile reagent for the radical version of the Michael reaction
Foubelo,Lloret,Yus
, p. 9531 - 9536 (1992)
The homoenolic radical, derived from 3-iodopropionic acid (1) by reaction with in situ generated tributyltin hydride, undergoes clean carbon-carbon forming reaction with electrophilic olefins (2) yielding functionalized acids (3).
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Anderson,Wang
, p. 277,281 (1954)
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Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation
Sang, Rui,Kucmierczyk, Peter,Dühren, Ricarda,Razzaq, Rauf,Dong, Kaiwu,Liu, Jie,Franke, Robert,Jackstell, Ralf,Beller, Matthias
supporting information, p. 14365 - 14373 (2019/09/06)
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.
Pd-Catalyzed Highly Chemo- And Regioselective Hydrocarboxylation of Terminal Alkyl Olefins with Formic Acid
Ren, Wenlong,Chu, Jianxiao,Sun, Fei,Shi, Yian
supporting information, p. 5967 - 5970 (2019/08/26)
An efficient Pd-catalyzed hydrocarboxylation of alkenes with HCOOH is described. A wide variety of linear carboxylic acids bearing various functional groups can be obtained with excellent chemo- and regioselectivities under mild reaction conditions. The reaction process is operationally simple and requires no handling of toxic CO.
