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