期刊
CHEMICAL COMMUNICATIONS
卷 48, 期 87, 页码 10704-10714出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc34659a
关键词
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资金
- MEXT
- JSPS, Japan
- Grants-in-Aid for Scientific Research [22106526] Funding Source: KAKEN
Some new types of copper-mediated intermolecular oxidative direct C-C (hetero)aromatic cross-couplings are described. A combination of the simple CuCl2 salt and molecular oxygen allows 1,3-azoles to couple with terminal alkynes directly to form the corresponding heteroarylacetylenes. This direct version of Sonogashira-type coupling can be applied to the reaction with polyfluoroarenes. A copper acetate complex enables direct biaryl coupling between 2-arylazines and 1,3-azoles even in the absence of any palladium catalysts. Moreover, the Cu-based protocol can be extended to the coupling with indoles and pyrroles, in which a catalytic variant is also possible by using an ideal co-oxidant, atmospheric oxygen. On the other hand, a copper-promoted annulative direct coupling of o-alkynylphenols and -anilines with 1,3-azoles can provide a unique dehydrogenative approach to C3-azolylbenzoheteroles from nonhalogenated and nonmetalated starting materials. In addition, a related N-azolylindole synthesis from similar substrates is also disclosed.
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