Copper-catalyzed selective arylations of benzoxazoles with aryl iodides
Donghae Kim1, Kwangho Yoo1, Se Eun Kim1
1†Department of Chemistry and BK21Plus Research Team, Chungbuk National University, 1 Chungdae-ro, Seowon-gu, Cheongju-si, Chungbuk 362-763, Republic of Korea.
Abstract:
A copper-catalyzed direct ring-opening double N-arylation of benzoxazoles with aryl iodides has been developed. The present system exhibits high selectivity despite competition from C-arylation. The selectivity between ring-opening N-arylation and C-arylation was controlled by the choice of reaction vessel. The nitrile bound bis(triphenylphosphine)copper cyanide was identified as the active catalytic species for both reactions, and when combined with a nitrile-containing solvent, enhanced the reaction efficiency.
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