A simple method for the preparation of arylselanyl anilines

References

• Tingoli, M.; Diana, R.; Panunzi, B. N-Phenylselenosaccharin (NPSSac): a New Electrophilic Selenium-Containing Reagent. Tetrahedron. Lett. 2006, 47, 7529. DOI: 10.1016/j.tetlet.2006.08.068.
   Web of Science ®Google Scholar
• Gassman, P. G.; Miura, A.; Miura, T. Direct Selenation of Electron-Rich Aromatic Compounds with (Phenylseleno)Dimethylsulfonium Tetrafluoroborate. J. Org. Chem. 1982, 47, 951. DOI: 10.1021/jo00345a010.
   Web of Science ®Google Scholar
• Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. New Approaches to the Synthesis of Unsymmetrical Diaryl Selenides. J. Organomet. Chem. 2000, 605, 96. DOI: 10.1016/S0022-328X(00)00265-5.
   Web of Science ®Google Scholar
• Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V. Russ. J. Org. Chem. 2001, 37, 1463. DOI: 10.1023/A:1013460213633.
   Web of Science ®Google Scholar
• Thurow, S.; Penteado, F.; Perin, G.; Jacob, R. G.; Alves, D.; Lenardão, E. J. Metal and Base-Free Synthesis of Arylselanyl Anilines Using Glycerol as a Solvent. Green Chem. 2014, 16, 3854. DOI: 10.1039/C4GC00874J.
   Web of Science ®Google Scholar
• Ricordi, V. G.; Thurow, S.; Penteado, F.; Schumacher, R.; Perin, G.; Lenardão, E. J.; Alves, D. Copper-Catalyzed Direct Arylselenation of Anilines by C–H Bond Cleavage. Adv. Synth. Catal. 2015, 357, 933. DOI: 10.1002/adsc.201400804.
   Web of Science ®Google Scholar
• Kumar, S.; Engman, L. Microwave-Assisted Copper-Catalyzed Preparation of Diaryl Chalcogenides. J. Org. Chem. 2006, 71, 5400. DOI: 10.1021/jo060690a.
   PubMed Web of Science ®Google Scholar
• Saba, S.; Rafique, J.; Braga, A. L. DMSO/Iodine-Catalyzed Oxidative C–Se/C–S Bond Formation: A Regioselective Synthesis of Unsymmetrical Chalcogenides with Nitrogen- or Oxygen-Containing Arenes. Catal. Sci. Technol. 2016, 6, 3087. DOI: 10.1039/C5CY01503K.
   Web of Science ®Google Scholar
• Yu, C.; Shi, H.-W.; Zhu, M.; Yan, J. A Convenient Catalytic Procedure for Direct Synthesis of ArylSelanyl Anilines. Synlett. 2015, 26, 2139.
   Web of Science ®Google Scholar
• Saba, S.; Rafique, J.; Franco, M. S.; Schneider, A. R.; Espíndola, L.; Silva, D. O.; Braga, A. L. Rose Bengal Catalysed photo-induced selenylation of indoles, imidazoles and arenes: a metal free approach . Org. Biomol. Chem. 2018, 16, 880 DOI: 10.1039/C7OB03177G.
   PubMed Web of Science ®Google Scholar
• Uyanik, M.; Okamoto, H.; Yasui, T.; Ishihara, K. Quaternary Ammonium (hypo)iodite catalysis for enantioselective oxidative cycloetherification. Science. 2010, 328, 1376 DOI: 10.1126/science.1188217.
   PubMed Web of Science ®Google Scholar
• Yang, K.; Ke, M.; Lin, Y.; Song, Q. Sulfonamide Formation from Sodium Sulfinates and Amines or Ammonia under Metal-Free Conditions at Ambient Temperature. Green Chem. 2015, 17, 1395. DOI: 10.1039/C4GC02236J.
   Web of Science ®Google Scholar
• Duan, Y.-N.; Zhang, Z.; Zhang, C. Recyclable Hypervalent-Iodine-Mediated Dehydrogenative Cyclopropanation under Metal-Free Conditions. Org. Lett. 2016, 18, 6176 DOI: 10.1021/acs.orglett.6b03209.
   PubMed Web of Science ®Google Scholar
• Siddaraju, Y.; Prabhu, K. R. Iodine Promoted Regioselective α-Sulfenylation of Carbonyl Compounds Using Dimethyl Sulfoxide as an Oxidant. Org. Lett. 2016, 18, 6090 DOI: 10.1021/acs.orglett.6b03084.
   PubMed Web of Science ®Google Scholar
• Vieira, A. A.; Azeredo, J. B.; Godoi, M.; Santi, C.; da Silva Júnior, E. N.; Braga, A. L. Catalytic Chalcogenylation under Greener Conditions: A solvent-free sulfur- and seleno-functionalization of olefins via I2/DMSO oxidant system. J. Org. Chem. 2015, 80, 2120 DOI: 10.1021/jo502621a.
   PubMed Web of Science ®Google Scholar
• Xu, D.-D.; Sun, W.-W.; Xie, Y.-L.; Liu, J.-K.; Liu, B.; Zhou, Y.-B.; Wu, B. Metal-Free Regioselective Hypervalent Iodine-Mediated C-2 and C-3 Difunctionalization of N-Substituted Indoles. J. Org. Chem. 2016, 81, 11081. DOI: 10.1021/acs.joc.6b02078.
   PubMed Web of Science ®Google Scholar
• Ambethkar, S.; Vellimalai, M.; Padmini, V.; Bhuvanesh, N. Iodine-Mediated C–N and C–S Bond Formation: regioselective Synthesis of Benzo[4,5]Imidazo[2,1-b]Thiazoles. New J. Chem. 2017, 41, 75. DOI: 10.1039/C6NJ02102F.
   Web of Science ®Google Scholar
• Huang, Z.-Z.; Huang, X.; Huang, Y.-Z. Synthesis of Acyl(Phenylselanyl)Methylidene(Triphenyl)-λ 5 -Arsanes and Their Wittig-Type Reactions. J. Chem. Soc. Perkin Trans. I. 1995, 95. DOI: 10.1039/P19950000095.
   Google Scholar