期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 87, 期 13, 页码 8525-8533出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00627
关键词
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资金
- European Union (European Social Fund-ESF) [MIS-5033021]
- European Regional Development Fund of the European Union
- Greek national funds through the Operational Program Competitiveness, Entrepreneurship and Innovation, under the call RESEARCH-CREATE-INNOVATE) [T2EDeltaK-02364]
Au nanoparticles supported on TiO2 efficiently catalyze the hydration/6-endo cyclization of skipped diynones, leading to the formation of gamma-pyrones in aqueous dioxane. The reaction proceeds via triple bond activation, bypassing the formation of isomeric 3(2H)-furanones through a competing 5-exo cyclization pathway and the initial 1,3-transposition of the skipped diynones.
Supported Au nanoparticles on TiO2 catalyze the hydration/6-endo cyclization of skipped diynones to gamma-pyrones in aqueous dioxane, via triple bond activation. The isomeric 3(2H)-furanones which could be formed through a competing and often prevailing 5-exo cyclization pathway using homogeneous ionic Au(I) catalysts were not seen. The reaction does not proceed via the initial 1,3-transposition of the skipped diynones to their corresponding conjugated 1,3-diynone isomers. If aqueous methylamine is added, N-methyl-4-pyridones are exclusively formed in 69-79% yields via an analogous hydroamination/Au-catalyzed 6-endo cyclization pathway.
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