Transition-metal-free synthesis of thiocyanato- or nitro-arenes through diaryliodonium salts

References

• For some examples of bioactive compounds containing SCN groups, see (a) Hill, H. A. O. In Chemistry and Biochemistry of Thiocyanic Acid and Its Derivatives; A. A. Newman (Ed.); Academic Press: London, 1975; (b) Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujvary, I.; Szajnman, S. H.; Rodriguez, J. B. J. Med. Chem. 2002, 45, 3984; (c) Dutta, S.; Abe, H.; Aoyagi, S.; Kibayashi, C.; Gates, K. S. J. Am. Chem. Soc. 2005, 127, 15004; (d) Pasquini, S.; Mugnaini, C.; Tintori, C.; Botta, M.; Trejos, A.; Arvela, R. K.; Larhed, M.; Witvrouw, M.; Michiels, M.; Christ, F.; Debyser, Z.; Corelli, F. J. Med. Chem. 2008, 51, 5125.
   Google Scholar
• For some examples of bioactive compounds containing NO2 groups, see (a) Priestap, H. A.; De los Santos, C.; Quirke, J. M. J. Nat. Prod. 2010, 73, 1979; (b) Piechowska, J.; Huttunen, K.; Wróbel, Z.; Lemmetyinen, H.; Tkachenko, N. V.; D. Gryko, T. J. Phys. Chem. A 2012, 116, 9614; (c) Sosič, I.; Mirković, B.; Arenz, K.; Štefane, B.; Kos, J.; Gobec, S. J. Med. Chem. 2013, 56, 521; (d) Tiwari, R.; Moraski, G. C.; KrchňáK, V.; Miller, P. A.; Colon-Martinez, M.; Herrero, E.; Oliver, A. G.; Miller, M. J. J. Am. Chem. Soc. 2013, 135, 3539.
   PubMed Web of Science ®Google Scholar
• (a) Alcaraz, M. L.; Atkinson, S. P.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; Noble, A. J.; O’Beirne, D.; Patel, Z. M.; Perkins, J.; Rowan, P.; Sadler, P.; Singleton, J. T.; Tornos, J.; Watts, A. J.; Woodland, I. A. Org. Process Res. Dev. 2005, 9, 555; (b) Pasquini, S.; Mugnaini, C.; Tintori, C.; Botta, M.; Trejos, A.; Arvela, R. K.; Larhed, M.; Witvrouw, M.; Michiels, M.; Christ, F.; Debyser, Z.; Corelli, F. J. Med. Chem. 2008, 51, 5125; (c) Asif, M. PharmaTutor 2015, 3, 15; (d) Colón, I. G.; González, F. A.; Cordero, M.; Zayas, B.; Velez, C.; Cox, O.; Kumar, A.; Alegría, A. E. Chem. Res. Toxicol. 2008, 21, 1706.
   Web of Science ®Google Scholar
• For some recent examples of formation of SCN groups, see (a) Grant, M. S.; Snyder, H. R. J. Am. Chem. Soc. 1960, 82, 2742; (b) Toste, F. D.; De Stefano, V.; Still, I. W. J. Synth. Commun. 1995, 25, 1277; (c) Prakash, O.; Kaur, H.; Batra, H.; Rani, N.; Singh, S. P.; Moriarty, R. M. J. Org. Chem. 2001, 66, 2019; (d) Bhalerao, D. S.; Akamanchi, K. G. Synlett 2007, 2007, 2952; (e) Yadav, J. S.; Reddy, B. V. S.; Murali Krishna, B. B. Synthesis 2008, 2008, 3779; (f) Fan, W.; Yang, Q.; Xu, F.; Li, P. J. Org. Chem. 2014, 79, 10588; (g) Zhu, D.; Chang, D.; Shi, L. Chem. Commun. 2015, 51, 7180; (h) Frei, R.; Courant, R.; Wodrich, M. D.; Waser, J. Chem. Eur. J. 2015, 21, 2662; (i) Tang, F.; Yu, J. T.; Yang, H. T.; Jiang, Y.; Cheng, J. Chem. Commun. 2014, 50, 12139.
   Web of Science ®Google Scholar
• For some recent examples of formation of NO2 groups, see (a) Yan, G. B.; Yang, M. H. Org. Biomol. Chem. 2013, 11, 2554; (b) Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 12898; (c) Manna, S.; Maity, S.; Rana, S.; Agasti, S.; Maiti, D. Org. Lett. 2012, 14, 1736; (d) Zhang, W.; Lou, S. J.; Liu, Y. K.; Xu, Z. Y. J. Org. Chem. 2013, 78, 5932; (e) Zhang, W.; Zhang, J.; Ren, S. B.; Liu, Y. K. J. Org. Chem. 2014, 79, 11508; (f) Zhang, W.; Ren, S. B.; Zhang, J.; Liu, Y. K. J. Org. Chem. 2015, 80, 5973; (g) Liang, Y. F.; Li, X. Y.; Wang, X. Y.; Yan, Y. P.; Feng, P.; Jiao, N. ACS Catal. 2015, 5, 1956; (h) Liu, J.; Li, J.; Ren, J. M.; Zeng, B. B. Tetrahedron Lett. 2014, 55, 1581.
   PubMed Web of Science ®Google Scholar
• (a) Guy, G. R. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S. (Ed.); John Wiley & Sons: New York, 1977; part 2, p. 819; (b) Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 8275; (c) De Mico, A.; Margarita, R.; Mariani, A.; Piancatelli, G. Chem. Commun. 1997, 13, 1237; (c) Maxwell, R. J.; Silbert, L. S.; Russell, J. R. J. Org. Chem. 1977, 42, 1510; (d) Zhu, N.; Wang, F.; Chen, P. H.; Ye, J. X.; Liu, G. S. Org. Lett. 2015, 17, 3580; (e) Liang, Z. L.; Wang, F.; Chen, P. H.; Liu, G. S. Org. Lett. 2015, 17, 2438; (f) Yang, H.; Duan, X. H.; Zhao, J. F.; Guo, L. N. Org. Lett. 2015, 17, 1998.
   Google Scholar
• For examples of thioethers, see (a) Still, I. W. J.; Toste, F. D. J. Org. Chem. 1996, 61, 7677; (b) Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 454; For examples of disulfides, see (c) Prabhu, K. R.; Ramesha, A. R.; Chandrasekaran, S. J. Org. Chem. 1995, 60, 7142; (d) Sengupta, D.; Basu, B. Tetrahedron Lett. 2013, 54, 2277; For examples of thiols, see (e) Houk, J.; Whitesides, G. M. J. Am. Chem. Soc. 1987, 109, 6825; (f) Linderoth, L.; Fristrup, P.; Hansen, M.; Melander, F.; Madsen, R.; Andresen, T. L.; Peters, G. H. J. Am. Chem. Soc. 2009, 131, 12193; For examples of other sulfur compounds, see (g) Pawliczek, M.; Garve, L. K. B.; Werz, D. B. Org. Lett. 2015, 17, 1716.
   PubMed Web of Science ®Google Scholar
• (a) Wood, J. L.; Fieser, L. F. J. Am. Chem. Soc. 1941, 63, 2323; (b) Pilgram, K.; Phillips, D. D. J. Org. Chem. 1965, 30, 2388.
   Google Scholar
• Wang, Y. E.; Zhou, Y.; Wang, J. R.; Liu, L.; Guo, Q. X. Chin. Chem. Lett. 2006, 17, 1283.
   Web of Science ®Google Scholar
• (a) Takagi, K.; Takachi, H.; Sasaki, K. J. Org. Chem. 1995, 60, 6552; (b) Sun, N.; Che, L. S.; Mo, W. M.; Hu, B. X.; Shen, Z. L.; Hu, X. Q. Org. Biomol. Chem. 2015, 13, 691.
   Web of Science ®Google Scholar
• (a) Still, I. W. J.; Watson, I. D. G. Synth. Commun. 2011, 31, 1355; (b) Wang, Z. H.; Ji, X. M.; Hu, M. L.; Tang, R. Y. Tetrahedron Lett. 2015, 56, 5067.
   Web of Science ®Google Scholar
• Transition-metal-free arylation examples, see (a) Ravi, M.; Chauhan, P.; Kant, R.; Shukla, S. K.; Yadav, R. P. J. Org. Chem. 2015, 80, 5369; (b) Wang, D. W.; Ge, B. Y.; Li, L.; Shan, J.; Ding, Y. Q. J. Org. Chem. 2014, 79, 8607; (c) Bhojgude, S. S.; Kaicharla, T.; Biju, A. T. Org. Lett. 2013, 15, 5452; (d) Basavanag, U. M. V.; Dos Santos, A.; El Kaim, L.; Gamez-Montano, R.; Grimaud, L. Angew. Chem. Int. Ed. 2013, 52, 7194; (e) Gao, H. Y.; Ess, D. H.; Yousufuddin, M.; Kürti, L. J. Am. Chem. Soc. 2013, 135, 7086; (f) Chen, W. C.; Hsu, Y. C.; Shih, W. C.; Lee, C. Y.; Chuang, W. H.; Tsai, Y. F.; Chen, P. P. Y.; Ong, T. G. Chem. Commun. 2012, 48, 6702.
   PubMed Web of Science ®Google Scholar
• For a review of transition-metal-free arylation with diaryliodonium salts, see Merritt, E. A.; Olofsson, B. Angew. Chem. Int. Ed. 2009, 48, 9052.
   PubMed Web of Science ®Google Scholar
• For some examples for synthesis of diaryliodonium salts, see (a) Bielawski, M.; Aili, D.; Olofsson, B. J. Org. Chem. 2008, 73, 4602; (b) Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610.
   PubMed Web of Science ®Google Scholar
• For some examples of O- or N-arylation process, see (a) Dey, C.; Lindsted, E.; Olofsson, B. Org. Lett. 2015, 17, 4554; (b) Monastyrskyi, A.; Namelikonda, N. K.; Manestsch, R. J. Org. Chem. 2015, 80, 2513; (c) Lindstedt, E.; Ghosh, R.; Olofsson, B. Org. Lett. 2013, 15, 6070; (d) Ghosh, R.; Olofsson, B. Org. Lett. 2014, 16, 1830; (e) Gao, H. Y.; Xu, Q. L.; Keene, C.; Kürti, L. Chem. Eur. J. 2014, 20, 8883; (f) Ghosh, R.; Stridfeldt, E.; Olofsson, B. Chem. Eur. J. 2014, 20, 8888; (g) Yang, Y.; Wu, X. S.; Han, J. W.; Mao, S.; Qian, X. F.; Wang, L. M. Eur. J. Org. Chem. 2014, 2014, 6854; (h) Guo, F. L.; Wang, L. M.; Wang, P. Q.; Yu, J. J.; Han, J. W. Asian J. Org. Chem. 2012, 1, 218; (i) Jalalian, N.; Petersen, T. B.; Olofsson, B. Chem. Eur. J. 2012, 18, 14140.
   PubMed Web of Science ®Google Scholar
• (a) Lubinkowski, J. J.; Gomez, M.; Calderon, J. L.; McEwen, W. E. J. Org. Chem. 1978, 43, 2432; (b) Wang, B. J.; Graskemper, J. W.; Qin, L. L.; Dimagno, S. G. Angew. Chem. Int. Ed. 2010, 49, 4079; (c) Yusubov, M. S.; Svitich, D. Y.; Yoshimura, A.; Kastern, B. J.; Nemylin, V. N.; Zhdankin, V. V. Eur. J. Org. Chem. 2015, 4831.
   Web of Science ®Google Scholar
• (a) Ma, X. P.; Shi, W. M.; Mo, X. L.; Li, X. H.; Li, L. G.; Pan, C. X.; Chen, B.; Su, G. F.; Mo, D. L. J. Org. Chem. 2015, 80, 10098; (b) Shi, W. M.; Ma, X. P.; Pan, C. X.; Su, G. F.; Mo, D. L. J. Org. Chem. 2015, 80, 11175.
   PubMed Web of Science ®Google Scholar
• When unsymmetric diaryliodonium salts were used, some of the desired products were obtained in lower yields because the other aryl moieties were also transferred to the thiocyanatoarenes and the yields were 5–15%. For studies on the chemoselectivity on diaryliodonium salts, see Malmgren, J.; Santoro, S.; Jalalian, N.; Himo, F.; Olofsson, B. Chem. Eur. J. 2013, 19, 10334.
   PubMed Web of Science ®Google Scholar
• Saravanan, P.; Anbarasan, P. Org. Lett. 2014, 16, 848.
   PubMed Web of Science ®Google Scholar
• Kumar, S.; Rathore, V.; Verma, A.; Prasad, C. D.; Kumar, A.; Yadav, A.; Jana, S.; Meenakshi, M. S.; Kumar, S. Org. Lett. 2015, 17, 82.
   PubMed Web of Science ®Google Scholar