Palladium-catalyzed carbonylation of aryl bromides and iodides with potassium phenoxides

Autor:	Taka Aki Hanaoka, Yoshihiro Kubota, Kazuhiko Takeuchi, Yoshihiro Sugi
Rok vydání:	1996
Předmět:	Steric effects Reaction mechanism Process Chemistry and Technology Aryl chemistry.chemical_element Halide Medicinal chemistry Catalysis Reductive elimination chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry Carbonylation Palladium
Zdroj:	Journal of Molecular Catalysis A: Chemical. 111:L187-L192
ISSN:	1381-1169
Popis:	Palladium-catalyzed aryloxycarbonylation of aryl bromides and iodides show contrastive reactivities with respect to the kind of phenoxides. The carbonylation of bromides with hindered potassium phenoxides in benzene gives ester products in high yields, while that with non-hindred PhOK gives almost no ester product under the same conditions. In contrast, the carbonylation of iodides with hindered potassium phenoxides gives no ester, while that with non-hindered PhOK provides ester products in high yields. Variant reductive elimination steps from aroyl palladium halide species to ester products and Pd(0) species are proposed depending on the steric and electronic properties of the phenoxides and aryl halides. They involve a stepwise ligand exchange path and a concerted path.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c3aad2843ca1382abfdb33439f7c5f2c https://doi.org/10.1016/1381-1169(96)00217-8 Zobrazit plný text záznamu Full Text from ScienceDirect