Acid-base-sensitive allylic oxidation of 2-allylbenzoic acids to form phthalides

Le Thi Ngoc Chuc, Thi Anh Hong Nguyen, Duen Ren Hou

研究成果: 雜誌貢獻期刊論文同行評審

6 引文 斯高帕斯(Scopus)

摘要

Allylic oxidation of 2-allylbenzoic acids to phthalides, instead of Wacker-type isocoumarins, was achieved with 1,2-bis(phenylsulfinyl)ethane palladium(ii) acetate (White catalyst) and oxygen in DMSO. The selective formation of 3-ethylidenephthalides or 3-vinylphthalides was controlled by the addition of acids or bases, and the reaction conditions were applied to substituted 2-allylbenzoic acids to generate corresponding phthalides selectively. Mechanistic studies, including the corresponding reaction of (E)-2-(1-propenyl)benzoic acid to 3-methylisocoumarin, isomerization reaction of 3-vinylphthalide to 3-ethylidenephthalide, and the kinetic isotope effect using 2-(1,1-d2-allyl)benzoic acid, revealed the competition between Wacker-type oxidation and allylic C-H cleavage, which is the key step to generating phthalides. A natural product, 3-ethyl-6-hydroxyphthalide, was prepared by this method.

原文???core.languages.en_GB???
頁(從 - 到)2758-2768
頁數11
期刊Organic and Biomolecular Chemistry
18
發行號14
DOIs
出版狀態已出版 - 14 4月 2020

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