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A general method for copper-catalyzed arylation of arene C-H bonds.

ABSTRACT: A general method for copper-catalyzed arylation of sp (2) C-H bonds with p K a's below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K 3PO 4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper-phenanthroline complex intermediates were independently synthesized.

SUBMITTER: Do HQ

PROVIDER: S-EPMC2740489 | biostudies-other | 2008 Nov

REPOSITORIES: biostudies-other

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A general method for copper-catalyzed arylation of arene C-H bonds.

Do Hien-Quang HQ Khan Rana M Kashif RM Daugulis Olafs O

Journal of the American Chemical Society 20081015 45

A general method for copper-catalyzed arylation of sp (2) C-H bonds with p K a's below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K 3PO 4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups ...[more]

PMID: 18855471

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