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.
A general method for copper-catalyzed arylation of n class="Chemical">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.
Authors: Shinya Usui; Yuichi Hashimoto; James V Morey; Andrew E H Wheatley; Masanobu Uchiyama Journal: J Am Chem Soc Date: 2007-11-16 Impact factor: 15.419
Authors: Jesse W Tye; Zhiqiang Weng; Adam M Johns; Christopher D Incarvito; John F Hartwig Journal: J Am Chem Soc Date: 2008-07-03 Impact factor: 15.419
Authors: Ian B Seiple; Shun Su; Rodrigo A Rodriguez; Ryan Gianatassio; Yuta Fujiwara; Adam L Sobel; Phil S Baran Journal: J Am Chem Soc Date: 2010-09-29 Impact factor: 15.419