Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation.

作者: Fumitoshi Kakiuchi , Takuya Kochi , Hitoshi Mutsutani , Noboru Kobayashi , Seiya Urano

DOI: 10.1021/JA9049228

关键词: Combinatorial chemistryPalladiumElectrochemistryChemistryHalonium ionCatalysisHydrogen halideAqueous solutionPhotochemistryBond cleavageHalogenation

摘要: … , because they would enable direct C−H halogenation without generating organic byproducts. Herein we report palladium-catalyzed halogenation of aromatic C−H bonds with hydrogen …

参考文章(29)
Dipannita Kalyani, Melanie S. Sanford, Chelate-Directed Oxidative Functionalization of Carbon–Hydrogen Bonds: Synthetic Applications and Mechanistic Insights Topics in Organometallic Chemistry. ,vol. 24, pp. 85- 116 ,(2007) , 10.1007/3418_2007_068
Xiaobing Wan, Zhongxun Ma, Bijie Li, Keya Zhang, Shaokui Cao, Shiwei Zhang, Zhangjie Shi, Highly Selective C−H Functionalization/Halogenation of Acetanilide Journal of the American Chemical Society. ,vol. 128, pp. 7416- 7417 ,(2006) , 10.1021/JA060232J
W. C. Peter Tsang, Nan Zheng, Stephen L. Buchwald, Combined C-H functionalization/C-N bond formation route to carbazoles. Journal of the American Chemical Society. ,vol. 127, pp. 14560- 14561 ,(2005) , 10.1021/JA055353I
Anny Jutand, Contribution of Electrochemistry to Organometallic Catalysis Chemical Reviews. ,vol. 108, pp. 2300- 2347 ,(2008) , 10.1021/CR068072H
André B. Charette, Short cuts to complexity Nature. ,vol. 456, pp. 452- 453 ,(2008) , 10.1038/456451A
Allison R. Dick, Kami L. Hull, Melanie S. Sanford, A Highly Selective Catalytic Method for the Oxidative Functionalization of C−H Bonds Journal of the American Chemical Society. ,vol. 126, pp. 2300- 2301 ,(2004) , 10.1021/JA031543M
Tsutomu Inokuchi, Liu Ping, Fumihiro Hamaue, Miyoko Izawa, Sigeru Torii, Electrochemical Wacker Type Reaction with a Double Mediatory System Consisting of Palladium Complex and Tri(4-bromophenyl)amine Chemistry Letters. ,vol. 23, pp. 121- 124 ,(1994) , 10.1246/CL.1994.121
Kami L. Hull, Waseem Q. Anani, Melanie S. Sanford, Palladium-Catalyzed Fluorination of Carbon−Hydrogen Bonds Journal of the American Chemical Society. ,vol. 128, pp. 7134- 7135 ,(2006) , 10.1021/JA061943K
Hung-Yat Thu, Wing-Yiu Yu, Chi-Ming Che, Intermolecular Amidation of Unactivated sp2 and sp3 C−H Bonds via Palladium-Catalyzed Cascade C−H Activation/Nitrene Insertion Journal of the American Chemical Society. ,vol. 128, pp. 9048- 9049 ,(2006) , 10.1021/JA062856V
Kami L. Hull, Melanie S. Sanford, Catalytic and Highly Regioselective Cross-Coupling of Aromatic C−H Substrates Journal of the American Chemical Society. ,vol. 129, pp. 11904- 11905 ,(2007) , 10.1021/JA074395Z