期刊
ACS CATALYSIS
卷 7, 期 7, 页码 4242-4247出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00784
关键词
gold catalysis; noncarbene model; alkylidenecyclopropane-containing 1,5-enynes; 3,5-dibromo-pyridine N-oxide; polycyclic aromatic hydrocarbons
资金
- National Basic Research Program of China [(973)-2015CB856603]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- National Natural Science Foundation of China [20472096, 21372241, 21572052, 20672127, 21421091, 21372250, 21121062, 21302203, 20732008]
- Fundamental Research Funds for the Central Universities [222201717003]
A gold-catalyzed tandem cyclization oxidation of alkylidenecyclopropane-containing 1,5-enynes with 3,5-dibromo-pyridine N-oxide via a noncarbene model was developed, providing a range of synthetically valuable and useful arylacetaldehyde derivatives in moderate to good yields without oxidation of alkynes. Moreover, the corresponding aldehydes can be further transformed into polycyclic aromatic hydrocarbons in the presence of a catalytic amount of Lewis acid In(OTf)(3). The reaction represents an example of gold-catalyzed halide-free Kornblum-type oxidation through the oxidation of the cyclopropane moiety.
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