Silver(I)-mediated oxidative C(sp3)–H amination of ethers with azole derivatives under mild conditions

作者: Xiaoyu Wu , Kai Qiao , Hong Qin , Dong Zhang , Di Gao

DOI: 10.1039/C9QO00644C

关键词:

摘要: A silver(I)-mediated oxidative N–H/C(sp3)–H coupling of NH-azoles with ethers has been developed. Various substrates were well N-alkylated in this methodology and the corresponding desired products given moderate to good yields. Moreover, late-stage alkylation bioactive molecules was achieved. This protocol involved C(sp3)–N bond formation via a radical pathway generated presence low cost readily available heptafluoroisopropyl iodide (i-C3F7I). Generally, reaction features excellent functional group compatibility, broad substrate scope, regioselectivity, fast access pharmaceuticals such as SQ 22536.

参考文章(67)
Qingjing Yang, Pui Ying Choy, Wai Chung Fu, Baomin Fan, Fuk Yee Kwong, Copper-Catalyzed Oxidative C-H Amination of Tetrahydrofuran with Indole/Carbazole Derivatives. Journal of Organic Chemistry. ,vol. 80, pp. 11193- 11199 ,(2015) , 10.1021/ACS.JOC.5B01990
So Won Youn, Tae Yun Ko, Min Jung Jang, Su San Jang, Silver(I)-Mediated CH Amination of 2-Alkenylanilines: Unique Solvent-Dependent Migratory Aptitude Advanced Synthesis & Catalysis. ,vol. 357, pp. 227- 234 ,(2015) , 10.1002/ADSC.201400759
David P. Richardson, Gordon S. Bauer, Andrew A. Bravo, Michael Drzyzga, Tina Motazedi, Emma M. Pelegri-O’Day, Shirish Poudyal, Daniel L.M. Suess, John W. Thoman, A convenient and practical method for the selective preparation of deuterofluorocarbons Journal of Fluorine Chemistry. ,vol. 180, pp. 208- 215 ,(2015) , 10.1016/J.JFLUCHEM.2015.10.002
Thomas D. Penning, Gui-Dong Zhu, Viraj B. Gandhi, Jianchun Gong, Sheela Thomas, Wilfried Lubisch, Roland Grandel, Wolfgang Wernet, Chang H. Park, Elizabeth H. Fry, Xuesong Liu, Yan Shi, Vered Klinghofer, Eric F. Johnson, Cherrie K. Donawho, David J. Frost, Velitchka Bontcheva-Diaz, Jennifer J. Bouska, Amanda M. Olson, Kennan C. Marsh, Yan Luo, Saul H. Rosenberg, Vincent L. Giranda, Discovery and SAR of 2-(1-propylpiperidin-4-yl)-1H-benzimidazole-4-carboxamide: A potent inhibitor of poly(ADP-ribose) polymerase (PARP) for the treatment of cancer. Bioorganic & Medicinal Chemistry. ,vol. 16, pp. 6965- 6975 ,(2008) , 10.1016/J.BMC.2008.05.044
Xiao-jun Wang, Kanwar Sidhu, Li Zhang, Scot Campbell, Nizar Haddad, Diana C. Reeves, Dhileepkumar Krishnamurthy, Chris H. Senanayake, Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: efficient synthesis of poly-substituted 1,2,3-triazoles. Organic Letters. ,vol. 11, pp. 5490- 5493 ,(2009) , 10.1021/OL902334X
Joon Seok Park, Kyung A Yu, Tae Hee Kang, Sunghoon Kim, Young-Ger Suh, Discovery of novel indazole-linked triazoles as antifungal agents. Bioorganic & Medicinal Chemistry Letters. ,vol. 17, pp. 3486- 3490 ,(2007) , 10.1016/J.BMCL.2007.03.074
Yun-Fei Li, Gui-Feng Wang, Pei-Lan He, Wei-Gang Huang, Feng-Hua Zhu, He-Yong Gao, Wei Tang, Yu Luo, Chun-Lan Feng, Li-Ping Shi, Yu-Dan Ren, Wei Lu, Jian-Ping Zuo, Synthesis and anti-hepatitis B virus activity of novel benzimidazole derivatives. Journal of Medicinal Chemistry. ,vol. 49, pp. 4790- 4794 ,(2006) , 10.1021/JM060330F
Masahito Ochiai, Shinichi Yamane, Md. Mahbubul Hoque, Motomichi Saito, Kazunori Miyamoto, Metal-free α-CH amination of ethers with hypervalent sulfonylimino-λ3-bromane that acts as an active nitrenoid. Chemical Communications. ,vol. 48, pp. 5280- 5282 ,(2012) , 10.1039/C2CC31523H
Armando Rossello, Simone Bertini, Annalina Lapucci, Marco Macchia, Adriano Martinelli, Simona Rapposelli, Esperanza Herreros, Bruno Macchia, Synthesis, Antifungal Activity, and Molecular Modeling Studies of New Inverted Oxime Ethers of Oxiconazole Journal of Medicinal Chemistry. ,vol. 45, pp. 4903- 4912 ,(2002) , 10.1021/JM020980T
Santiago E. Vaillard, Al Postigo, Roberto A. Rossi, Novel Perfluoroalkyl-Diphenylphosphine Compounds. Syntheses and Reaction Mechanisms Organometallics. ,vol. 23, pp. 3003- 3007 ,(2004) , 10.1021/OM034313P