期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 48, 页码 17092-17095出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja1086547
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资金
- NSF [CHE-0910641]
- NIH [GM087901]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1156496, 0910641] Funding Source: National Science Foundation
A strategy for the ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives has been developed in which a hydroxyl group formally serves as the directing element for Ir-catalyzed arene C-H bond activation. One-pot generation of a (hydrido)silyl ether from the carbonyl compound or alcohol is followed by dehydrogenative cyclization at 80-100 degrees C in the presence of norbornene as a hydrogen acceptor and the combination of 1 mol%[Ir(cod)OMe](2) and 1,10-phenanthroline as a catalyst to form benzoxasiloles. The synthetic utility of the benzoxasilole products is demonstrated by conversion to phenol or biaryl derivatives by Tamao-Fleming oxidation or Hiyama cross-coupling. Both of these transformations of the C-H silylation products exploit the Si-O bond in the system and proceed by activation of the silyl moiety with hydroxide, rather than fluoride.
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