期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 40, 页码 14175-14180出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201603055
关键词
allenes; diels-alder reaction; furans; gold catalysis; propargyl carbonates
资金
- National Natural Science Foundation of China [21372244, 21572256, 21421091]
- Chinese Academy of Science
Gold-catalyzed cyclization of various furan-ynes with a propargyl carbonate or ester moiety results in the formation of a series of polycyclic aromatic ring systems. The reactions can be rationalized through a tandem goldcatalyzed 3,3-rearrangement of the propargyl carboxylate moiety in furan-yne substrates to form an allenic intermediate, which is followed by an intramolecular DielsAlder reaction of furan and subsequent ring-opening of the oxa-bridged cycloadduct. It was found that the steric and electronic properties of phosphine ligands on the gold catalyst had a significant impact on the reaction outcome. In the case of 1,5-furan-yne, the cleavage of the oxa-bridge in the cycloadduct with concomitant 1,2-migration of the R-1 group occurs to furnish anthracen-1(2H)-ones bearing a quaternary carbon center. For 1,4-furanyne, a facile aromatization of the cycloadduct takes place to give 9-oxygenated anthracene derivatives.
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