1466-76-8Relevant articles and documents
The gold(I)-catalysed protodecarboxylation mechanism
Dupuy, St??phanie,Crawford, Luke,B??hl, Michael,Nolan, Steven P.
, p. 3399 - 3408 (2015)
A mechanistic study of the gold-catalysed protodecarboxylation is described. Each reaction step has been investigated experimentally and computationally. More specifically, the activation parameters for the decarboxylation step have been determined through kinetic studies. Further experimental studies on the hydrolysis of the arylgold intermediate have revealed that the protodeauration can become competitive with the decarboxylation process at high conversions. This switch in rate-limiting step has been shown to be pKa-dependent. These studies have been supported by DFT calculations and permit a better understanding of which prevalent features of the reaction mechanism account for the decarboxylation process.
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Screttas
, p. 869 (1972)
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Gilman et al.
, p. 667 (1940)
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Metal-Free Dehomologative Oxidation of Arylacetic Acids for the Synthesis of Aryl Carboxylic Acids
Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Shinde, Suresh L.,Chaskar, Atul C.
, p. 3781 - 3786 (2017/04/11)
A novel I2-promoted direct conversion of arylacetic acids into aryl carboxylic acids under metal-free conditions has been described. This remarkable transformation involves decarboxylation followed by an oxidation reaction enabled just by using DMSO as the solvent as well as an oxidant. Notably, aryl carboxylic acids are isolated by simple filtration technique and obtained in good to excellent yields. This protocol is free from chromatographic purification, which makes it applicable for large-scale synthesis.
