Palladium-Catalyzed Ortho-Arylation of Benzamides via Direct sp2 C–H Bond Activation
作者： Dan-Dan Li , Ting-Ting Yuan , Guan-Wu Wang
DOI: 10.1021/JO300126N
关键词: Chemistry 、 C h bond 、 Medicinal chemistry 、 Palladium 、 Organic chemistry 、 Biphenyl derivatives 、 Aryl 、 Amide 、 Group (periodic table) 、 Catalysis
摘要: The palladium-catalyzed ortho-arylation of benzamides by aryl iodides has been demonstrated with the simplest amide CONH2 as a directing group for first time. This protocol can be applied to various and both electron-donating electron-withdrawing groups. In addition, synthesized biphenyl-2-carboxamides further transformed other biphenyl derivatives such nitriles, carboxylic acids, carbamates, amines.
acs.org
sci-hub.se 参考文章(102)
Masayuki Wasa, Keary M. Engle, Jin-Quan Yu, Pd(0)/PR3-Catalyzed Intermolecular Arylation of sp3 C−H Bonds Journal of the American Chemical Society. ,vol. 131, pp. 9886- 9887 ,(2009) , 10.1021/JA903573P
Jinho Kim, Sukbok Chang, A new combined source of "CN" from N,N-dimethylformamide and ammonia in the palladium-catalyzed cyanation of aryl C-H bonds. Journal of the American Chemical Society. ,vol. 132, pp. 10272- 10274 ,(2010) , 10.1021/JA104917T
Keith Fagnou, Mechanistic considerations in the development and use of azine, diazine and azole N-oxides in palladium-catalyzed direct arylation. Topics in Current Chemistry. ,vol. 292, pp. 35- 56 ,(2009) , 10.1007/128_2009_14
Dong-Hui Wang, Keary M Engle, Bing-Feng Shi, Jin-Quan Yu, Ligand-Enabled Reactivity and Selectivity in a Synthetically Versatile Aryl C–H Olefination Science. ,vol. 327, pp. 315- 319 ,(2010) , 10.1126/SCIENCE.1182512
Paul Lloyd-Williams, Ernest Giralt, Atropisomerism, biphenyls and the Suzuki coupling: peptide antibiotics Chemical Society Reviews. ,vol. 30, pp. 145- 157 ,(2001) , 10.1039/B001971M
Kami L. Hull, Melanie S. Sanford, Mechanism of Benzoquinone-Promoted Palladium-Catalyzed Oxidative Cross-Coupling Reactions Journal of the American Chemical Society. ,vol. 131, pp. 9651- 9653 ,(2009) , 10.1021/JA901952H
Sambasivarao Kotha, Kakali Lahiri, Dhurke Kashinath, Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis Tetrahedron. ,vol. 58, pp. 9633- 9695 ,(2002) , 10.1016/S0040-4020(02)01188-2
Takashi Nishikata, Alexander R. Abela, Bruce H. Lipshutz, Room Temperature C ? H Activation and Cross‐Coupling of Aryl Ureas in Water Angewandte Chemie. ,vol. 49, pp. 781- 784 ,(2010) , 10.1002/ANIE.200905967
Dan-Dan Li, Ting-Ting Yuan, Guan-Wu Wang, Synthesis of isoindolinones via palladium-catalyzed C–H activation of N-methoxybenzamides Chemical Communications. ,vol. 47, pp. 12789- 12791 ,(2011) , 10.1039/C1CC15897J
Dmitry Shabashov, Olafs Daugulis, Palladium-catalyzed anilide ortho-arylation and subsequent one-pot cyclization to phenanthridines. Journal of Organic Chemistry. ,vol. 72, pp. 7720- 7725 ,(2007) , 10.1021/JO701387M