Visible-Light-Driven, One-pot Amide Synthesis Catalyzed by the B12 Model Complex under Aerobic Conditions.

作者: Hui Tian , Hisashi Shimakoshi , Toshikazu Ono , Yoshio Hisaeda

DOI: 10.1002/CPLU.201800522

关键词:

摘要: A visible light responsive catalytic system with the B12 complex as catalyst and [Ir(dtbbpy)(ppy)2 ]PF6 photosensitizer was developed. It provides a convenient efficient way to synthesize amides. Based on this method, trichlorinated organic compounds were converted into amides in presence of an amine under aerobic conditions at room temperature one-pot procedure. Various source, such primary, secondary, cyclic amines, have been evaluated for transformation, providing expected products moderate excellent yields. Notably, product formation depended reaction atmosphere where amide obtained while partially dechlorinated anaerobic conditions. As protocol is free from hazardous reagents, extra additives, noble metals, dangerous gas, present method novel approach synthesis mild easily controlled

参考文章(39)
Lucia Flamigni, Andrea Barbieri, Cristiana Sabatini, Barbara Ventura, Francesco Barigelletti, Photochemistry and Photophysics of Coordination Compounds: Iridium Springer, Berlin, Heidelberg. pp. 143- 203 ,(2007) , 10.1007/128_2007_131
Paul J. Toscano, Luigi G. Marzilli, B12and Related Organocobalt Chemistry: Formation and Cleavage of Cobalt Carbon Bonds Progress in Inorganic Chemistry. ,vol. 31, pp. 105- 204 ,(2007) , 10.1002/9780470166321.CH2
Hisashi Shimakoshi, Mami Tokunaga, Yoshio Hisaeda, Hydrophobic vitamin B12. Part 19: Electroorganic reaction of DDT mediated by hydrophobic vitamin B12 Dalton Transactions. ,vol. 4, pp. 878- 882 ,(2004) , 10.1039/B315170K
A. Juris, V. Balzani, F. Barigelletti, S. Campagna, P. Belser, A. von Zelewsky, Ru(II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence Coordination Chemistry Reviews. ,vol. 84, pp. 85- 277 ,(1988) , 10.1016/0010-8545(88)80032-8
Yukito Murakami, Yoshio Hisaeda, Akiro Kajihara, Hydrophobic vitamin B12. I. Preparation and axial ligation behavior of hydrophobic vitamin B12r. Bulletin of the Chemical Society of Japan. ,vol. 56, pp. 3642- 3646 ,(1983) , 10.1246/BCSJ.56.3642
Jagan M. R. Narayanam, Joseph W. Tucker, Corey R. J. Stephenson, Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction. Journal of the American Chemical Society. ,vol. 131, pp. 8756- 8757 ,(2009) , 10.1021/JA9033582
Wenting Wu, Zhihui Zhang, Lanny S. Liebeskind, In Situ Carboxyl Activation using a Silatropic Switch. A New Approach to Amide and Peptide Constructions Journal of the American Chemical Society. ,vol. 133, pp. 14256- 14259 ,(2011) , 10.1021/JA2065158
D. M. Schultz, T. P. Yoon, Solar Synthesis: Prospects in Visible Light Photocatalysis Science. ,vol. 343, pp. 1239176- 1239176 ,(2014) , 10.1126/SCIENCE.1239176
Jason D. Slinker, Alon A. Gorodetsky, Michael S. Lowry, Jingjing Wang, Sara Parker, Richard Rohl, Stefan Bernhard, George G. Malliaras, Efficient Yellow Electroluminescence from a Single Layer of a Cyclometalated Iridium Complex Journal of the American Chemical Society. ,vol. 126, pp. 2763- 2767 ,(2004) , 10.1021/JA0345221