NHC-Catalyzed Oxidative Cyclization Reactions of 2-Alkynylbenzaldehydes under Aerobic Conditions: Synthesis of O-Heterocycles

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139

초록

An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile as been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C-O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could be utilized as a source of an oxygen atom for the oxidation of aldehydes to the corresponding benzoic acids under our newly developed reagent system.

키워드

NUCLEOPHILIC CARBENES; AROMATIC-ALDEHYDES; IODOBENZOIC ACID; TERMINAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; CARBOXYLIC-ACIDS; COPPER-FREE; ISOCOUMARINS; EFFICIENT; ESTERIFICATION
제목
NHC-Catalyzed Oxidative Cyclization Reactions of 2-Alkynylbenzaldehydes under Aerobic Conditions: Synthesis of O-Heterocycles
저자
Park, Jong Hyub; Bhilare, Sachin V.; Youn, So Won
DOI
10.1021/ol200481u
발행일
2011-05
유형
Article
저널명
Organic Letters
권
13
호
9
페이지
2228 ~ 2231