Copper-catalyzed efficient dithiocyanation of styrenes: Synthesis of dithiocyanates

References

• (a) Grishchuk, B. D.; Prodanchuk, N. G.; Sinchenko, V. G.; Gorbovoi, P. M.; Kudrik, E. Y. Pharm. Chem. J. 1994, 28, 657–659; (b) Szajnman, S. H.; Yan, W.; Bailey, B. N.; Docampo, R.; Elhalem, E.; Rodriguez, J. B. J. Med. Chem. 2000, 43, 1826–1840; (c) Wood, J. L. Org. React. 1946, 3, 240–266; (d) Kelly, T. R.; Kim, M. H.; Curtis, A. D. M. J. Org. Chem. 1993, 58, 5855–5857.
   Google Scholar
• For a review, see Erian, A. W.; Sherif, S. M. Tetrahedron. 1999, 55, 7957–8024. For selected papers, see (a) Still, I. W. J.; Toste, D. F. J. Org. Chem. 1996, 61, 7677–7680; (b) Demko, Z. P.; Sharpless, B. K. Org. Lett. 2001, 3, 4091–4094; (c) Laufer, S. A.; Liedtke, A. J. Tetrahedron Lett. 2006, 47, 7199–7203; (d) Billard, T.; Langlois, B. R.; Medebielle, M. Tetrahedron Lett. 2001, 42, 3463–3465; (e) Garcia, P.; Evanno, Y.; George, P.; Sevrin, M.; Ricci, G.; Malacria, M.; Aubert, C.; Gandon, V. Chem. Eur. J. 2012, 18, 4337–4344; (f) Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 454–457; (g) Sureshbabu, V. V.; Vasantha, B.; Hemantha, H. P. Synthesis 2011, 9, 1447–1455; (h) Piekutowska, M.; Pakulski, Z. Tetrahedron Lett. 2007, 48, 8482–8486; (i) Zhang, Z.; Liebeskind, L. S. Org. Lett. 2006, 8, 4331–4333; (j) Zarchi, M. A. K.; Nahid, E. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 1226–1235.
   Web of Science ®Google Scholar
• (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285–2310; (b) Jensen, K. H.; Sigman, M. S. Org. Biomol. Chem. 2008, 6, 4083–4088; (c) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981–3019; (d) Francesca, C.; Goti, A. Nat. Chem. 2009, 1, 269–275; (e) Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294–8308; (f) Chemler, S. R.; Bovino, M. T. ACS Catal. 2013, 3, 1076–1091; (g) Muñiz, K.; Martínez, C. J. Org. Chem. 2013, 78, 2168–2174; (h) Huang, S.-X.; Ding, K.-L. Angew. Chem., Int. Ed. 2011, 50, 7734–7736; (i) Bataille, C. J. R.; Donohoe, T. J. Chem. Soc. Rev. 2011, 40, 114–128; (j) Minatti, A.; Muñiz, K. Chem. Soc. Rev. 2007, 36, 1142–1152; (k) Chen, D. J.; Timmons, C.; Wei, H. X.; Li, G. G. J. Org. Chem. 2003, 68, 5742–5745; (l) Wei, H. X.; Siruta, S.; Li, G. G. Tetrahedron Lett. 2002, 43, 3809–2812; (m) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483–2547; (n) Zhang, H. W.; Pu, W. Y.; Xiong, T.; Li, Y.; Zhou, X.; Sun, K.; Liu, Q.; Zhang, Q. Angew. Chem., Int. Ed. 2013, 52, 2529–2533; (o) Zhang, H. W.; Song, Y. C.; Zhao, J. B.; Zhang, J. P.; Zhang, Q. Angew. Chem., Int. Ed. 2014, 53, 11079–11083.
   PubMed Web of Science ®Google Scholar
• (a) Liang, Z. L.; Wang, F.; Chen, P. H.; Liu, G. S. Org. Lett. 2015, 17, 2438–2441; (b) Yang, H.; Duan, X. H.; Zhao, J. F.; Guo, L. N. Org. Lett. 2015, 17, 1998–2001; (c) Zhu, N.; Wang, F.; Chen, P. H.; Ye, J. X.; Liu, G. S. Org. Lett. 2015, 17, 3580–3583.
   PubMed Web of Science ®Google Scholar
• Mico, A. D.; Margarita, R.; Mariani, A.; Piancatelli, G. Chem. Commun. 1997, 13, 1237–1238.
   Google Scholar
• (a) Bruno, M.; Margarita, R.; Parlanti, L.; Piancatelli, G.; Trifoni, M. Tetrahedron Lett. 1998, 39, 3847–3848; (b) Mico, A. D.; Margarita, R.; Mariani, A.; Piancatelli, G. Tetrahedron Lett. 1996, 37, 1889–1892; (c) Nair, V.; Nair, L. G. Tetrahedron Lett. 1998, 39, 4585–4586; (d) Yadav, J. S.; Reddy, B. V. S.; Gupta, M. K. Synthesis 2004, 12, 1983–1986.
   Web of Science ®Google Scholar
• Chen, N. B.; Guo, S. S.; Guo, X.; Zhang, G. L.; Yu, Y. P. Org. Lett. 2015, 17, 4698–4701.
   PubMed Web of Science ®Google Scholar
• (a) He, Y. T.; Li, L. H.; Yang, Y. F.; Zhou, Z. Z.; Hua, H. L.; Liu, X. Y.; Liang, Y. M. Org. Lett. 2014, 16, 270–273; (b) llchenko, N. O.; Janson, P. G.; Szabó, K. J. J. Org. Chem. 2013, 78, 11087–11091.
   PubMed Web of Science ®Google Scholar