Copper-mediated oxidative direct C-C (hetero)aromatic cross-coupling.

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摘要：

Some new types of copper-mediated intermolecular oxidative direct C–C (hetero)aromatic cross-couplings are described. A combination of the simple CuCl2salt 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 ofo-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 relatedN-azolylindole synthesis from similar substrates is also disclosed.

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关键词：

organic chemistry, review C‐C bond formation general (heterocyclic compounds

DOI：

10.1039/c2cc34659a

被引量：

198

年份：

2012