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Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C−H Arylation of Unactivated Benzene

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posted on 2010-12-01, 00:00 authored by Wei Liu, Hao Cao, Hua Zhang, Heng Zhang, Kin Ho Chung, Chuan He, Haibo Wang, Fuk Yee Kwong, Aiwen Lei
A striking breakthrough to the frame of traditional cross-couplings/C−H functionalizations using an organocatalyst remains unprecedented. We uncovered a conceptually different approach toward the biaryl syntheses by using DMEDA as the catalyst to promote the direct C−H arylation of unactivated benzene in the presence of potassium tert-butoxide. The arylation of unactivated benzene with aryl iodides, or aryl bromides and even chlorides under the assistance of an iodo-group, could simply take place at 80 °C. The new methodology presumably involves an aryl radical anion as an intermediate. This finding offers an option toward establishing a new horizon for direct C−H/cross-coupling reactions.

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