Super electron donor-mediated reductive transformation of nitrobenzenes: a novel strategy to synthesize azobenzenes and phenazines
作者： Kanako Nozawa-Kumada , Erina Abe , Shungo Ito , Masanori Shigeno , Yoshinori Kondo
DOI: 10.1039/C8OB00271A
关键词: Chemistry 、 Nitrobenzene 、 Combinatorial chemistry 、 Transformation (music) 、 Electron donor 、 Reagent
摘要: The transformation of nitrobenzenes into azobenzenes by pyridine-derived super electron donor 2 is described. This method provides an efficient synthesis because not requiring the use expensive transition-metals, toxic or flammable reagents, harsh conditions. Moreover, when using 2-fluoronitrobenzenes as substrates, phenazines were found to be obtained. process affords a novel phenazines.
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sci-hub.se 参考文章(60)
Parisa Zaringhadam, Saeid Farhadi, Reza Zarei Sahamieh, Photo-assisted Oxidation of Anilines and Other Primary Aromatic Amines to Azo Compounds Using Mercury(II) Oxide as a Photo-Oxidant Acta Chimica Slovenica. ,vol. 54, pp. 647- 653 ,(2007)
Franziska Schoenebeck, John A. Murphy, Sheng-ze Zhou, Yoshitaka Uenoyama, Yves Miclo, Tell Tuttle, Reductive Cleavage of Sulfones and Sulfonamides by a Neutral Organic Super-Electron-Donor (S.E.D.) Reagent Journal of the American Chemical Society. ,vol. 129, pp. 13368- 13369 ,(2007) , 10.1021/JA074417H
Henry E. Baumgarten, Andris Staklis, Eileen M. Miller, Reactions of Amines. XIII. The Oxidation of N-Acyl-N-arylhydroxylamines with Lead Tetraacetate1,2 Journal of Organic Chemistry. ,vol. 30, pp. 1203- 1206 ,(1965) , 10.1021/JO01015A058
Bhimapaka China Raju, Kasagani Veera Prasad, Gannerla Saidachary, Balasubramanian Sridhar, A novel approach for C-C, C-N, and C-O bond formation reactions: a facile synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives via ring opening of benzoxepines. Organic Letters. ,vol. 16, pp. 420- 423 ,(2014) , 10.1021/OL4033122
John A. Murphy, Tanweer A. Khan, Sheng-ze Zhou, Douglas W. Thomson, Mohan Mahesh, Highly Efficient Reduction of Unactivated Aryl and Alkyl Iodides by a Ground-State Neutral Organic Electron Donor Angewandte Chemie International Edition. ,vol. 44, pp. 1356- 1360 ,(2005) , 10.1002/ANIE.200462038
Florian Hamon, Florence Djedaini-Pilard, Francis Barbot, Christophe Len, Azobenzenes—synthesis and carbohydrate applications Tetrahedron. ,vol. 65, pp. 10105- 10123 ,(2009) , 10.1016/J.TET.2009.08.063
Kazuo Takimiya, Tetsuya Jigami, Minoru Kawashima, Mie Kodani, Yoshio Aso, Tetsuo Otsubo, None, Synthetic Procedure for Various Selenium-Containing Electron Donors of the Bis(Ethylenedithio)tetrathiafulvalene (BEDT-TTF) Type The Journal of Organic Chemistry. ,vol. 67, pp. 4218- 4227 ,(2002) , 10.1021/JO016393H
John A. Murphy, Jean Garnier, Stuart R. Park, Franziska Schoenebeck, Sheng-ze Zhou, Andrew T. Turner, Super-Electron Donors: Bis-pyridinylidene Formation by Base Treatment of Pyridinium Salts Organic Letters. ,vol. 10, pp. 1227- 1230 ,(2008) , 10.1021/OL800134G
Ekta G. Ahuja, Petra Janning, Matthias Mentel, Almut Graebsch, Rolf Breinbauer, Wolf Hiller, Burkhard Costisella, Linda S. Thomashow, Dmitri V. Mavrodi, Wulf Blankenfeldt, PhzA/B Catalyzes the Formation of the Tricycle in Phenazine Biosynthesis Journal of the American Chemical Society. ,vol. 130, pp. 17053- 17061 ,(2008) , 10.1021/JA806325K
Yanina Moglie, Cristian Vitale, Gabriel Radivoy, Synthesis of azo compounds by nanosized iron-promoted reductive coupling of aromatic nitro compounds Tetrahedron Letters. ,vol. 49, pp. 1828- 1831 ,(2008) , 10.1016/J.TETLET.2008.01.053