21749-83-7Relevant articles and documents
Palladium-Catalyzed ?±-Arylation of Aryl Acetic Acid Derivatives via Dienolate Intermediates with Aryl Chlorides and Bromides
Sha, Sheng-Chun,Zhang, Jiadi,Walsh, Patrick J.
, p. 410 - 413 (2015)
To date, examples of ?±-arylation of carboxylic acids remain scarce. Using a deprotonative cross-coupling process (DCCP), a method for palladium-catalyzed ?3-arylation of aryl acetic acids with aryl halides has been developed. This protocol is applicable to a wide range of aryl bromides and chlorides. A procedure for the palladium-catalyzed ?±-arylation of styryl acetic acids is also described.
Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2
Yan, Si-Shun,Zhu, Lei,Ye, Jian-Heng,Zhang, Zhen,Huang, He,Zeng, Huiying,Li, Chao-Jun,Lan, Yu,Yu, Da-Gang
, p. 4873 - 4878 (2018/06/07)
The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2 to generate important aryl acetic acids is reported. Besides aldehyde hydrazones, a variety of ketone hydrazones, which have not been successfully applied in previous umpolung reactions with other reactive electrophiles, also show high reactivity and selectivity under mild conditions. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and offers easy derivation of important structures, including bioactive felbinac and adiphenine. Computational studies reveal that this umpolung reaction proceeds through the generation of a Ru-nitrenoid followed by concerted [4 + 2] cycloaddition with CO2.
Photostimulated reactions of phenylacetic acid dianions with aryl halides. Influence of the metallic cation on the regiochemistry of arylation.
Nwokogu,Wong,Greenwood,Wolfe
, p. 2643 - 2646 (2007/10/03)
[reaction: see text]Phenylacetic acid dianions react via what appears to be an S(RN)1 process with aryl halides under photostimulation to afford aryl substitution products 5 and 6. When the counterion is K+, only 4-biphenylacetic acids 5 are obtained. Both alpha- and para-coupling occurs with Na+ to give a mixture of 5 and 6, while exclusive formation of diphenylacetic acids 6 is observed with the dilithio salt of 1.