title: Organocatalysis in cross-coupling: DMEDA-catalyzed direct C-H arylation of unactivated benzene.
abstract: 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.
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, PR China.
authors.forename: Wei
authors.initials: W
authors.lastname: Liu
authors.forename: Hao
authors.initials: H
authors.lastname: Cao
authors.forename: Hua
authors.initials: H
authors.lastname: Zhang
authors.forename: Heng
authors.initials: H
authors.lastname: Zhang
authors.forename: Kin Ho
authors.initials: KH
authors.lastname: Chung
authors.forename: Chuan
authors.initials: C
authors.lastname: He
authors.forename: Haibo
authors.initials: H
authors.lastname: Wang
authors.forename: Fuk Yee
authors.initials: FY
authors.lastname: Kwong
authors.forename: Aiwen
authors.initials: A
authors.lastname: Lei
mesh_terms: D001554:Benzene / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D005029:Ethylenediamines / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*
chemical_list: D005029:Ethylenediamines; C091652:dioctyldiQAS; D002244:Carbon; D006859:Hydrogen; D001554:Benzene