期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 11, 页码 5530-5543出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo400613z
关键词
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资金
- JSPS
- MEXT
- Ritsumeikan Global Innovation Research Organization (R-GIRO)
- Asahi Glass Foundation
- NEDO of Japan
We have developed an efficient Bronsted acid-controlled strategy for the [3 + 2] coupling reaction of quinone monoacetals (QMAs) with nucleophilic alkenes, which is triggered by the particular use of a specific acid promoter, perfluorinated acid, and a solvent, fluoroalcohol. This new coupling reaction smoothly proceeded with high regiospecificity in regard with QMAs for introducing pi-nucleophiles to only the carbon alpha to the carbonyl group, thereby providing diverse dihydrobenzofurans and derivatives with high yields, up to quantitative, under mild conditions in short reaction times. The choice of Bronsted acid enabled us to avoid hydrolysis of the QMAs, which gives quinones, and the formation of discrete cationic species from the QMAs. Notably, further investigations in this study with regard to the acid have led to the findings that the originally stoichiometrically used acid could be reduced to a catalytic amount of 5 mol % loading or less and that the stoichiometry of the alkenes could be significantly improved down to only 1.2 equiv. The facts that only a minimal loading (5 mol %) of perfluoroterephthalic acid is required, readily available substrates can be used, and the regioselectivity can be controlled by the acid used make this coupling reaction very fascinating from a practical viewpoint.
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