Metal-Free Thiocyanation of Imidazoheterocycles through Visible Light Photoredox Catalysis

Journal of Organic Chemistry

Volumn 80, Issue 16, 2015, Pages 8275-8281

  Mitra, Shubhanjan ^a   Ghosh, Monoranjan ^a   Mishra, Subhajit ^a   Hajra, Alakananda ^a  

^a VISVA BHARATI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE;

AMBIENT AIR; EOSIN Y; HIGH YIELD; IMIDAZO[1 ,2-A]PYRIDINE; METAL FREE; PHOTOREDOX CATALYSIS; ROOM TEMPERATURE; VISIBLE LIGHT;

LIGHT;

EID: 84939807025     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01369     Document Type: Article

References (63)

1. Hari, D. P.; König, B. Angew. Chem., Int. Ed. 2013, 52, 4734 10.1002/anie.201210276
2. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
3. Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785 10.1002/anie.200904056
4. Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687 10.1039/c2cs35203f
5. Hering, T.; Hari, D. P.; König, B. J. Org. Chem. 2012, 77, 10347 10.1021/jo301984p
6. Rueping, M.; Vila, C.; Bootwicha, T. ACS Catal. 2013, 3, 1676 10.1021/cs400350j
7. Skubi, K. L.; Yoon, T. P. Nature 2014, 515, 45 10.1038/515045a
8. Xu, Z.; Gao, L.; Wang, L.; Gong, M.; Wang, W.; Yuan, R. ACS Catal. 2015, 5, 45 10.1021/cs5011037
9. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
10. Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97 10.1039/C2CS35250H
11. Huang, L.; Zhao, J. Chem. Commun. 2013, 49, 3751 10.1039/c3cc41494a
12. Guo, S.; Zhang, H.; Huang, L.; Guo, Z.; Xiong, G.; Zhao, J. Chem. Commun. 2013, 49, 8689 10.1039/c3cc44486d
13. Zhao, J.; Wu, W.; Sun, J.; Guo, S. Chem. Soc. Rev. 2013, 42, 5323 10.1039/c3cs35531d
14. Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355 10.1021/cs400956a
15. Ravelli, D.; Fagnoni, M. ChemCatChem 2012, 4, 169 10.1002/cctc.201100363
16. Cantillo, D.; de Frutos, O.; Rincón, J. A.; Mateos, C.; Kappe, C. O. Org. Lett. 2014, 16, 896 10.1021/ol403650y
17. Hari, D. P.; König, B. Chem. Commun. 2014, 50, 6688 10.1039/C4CC00751D
18. Kundu, D.; Ahammed, S.; Ranu, B. C. Org. Lett. 2014, 16, 1814 10.1021/ol500567t
19. Hari, D. P.; Schroll, P.; König, B. J. Am. Chem. Soc. 2012, 134, 2958 10.1021/ja212099r
20. Majek, M.; von Wangelin, A. J. Chem. Commun. 2013, 49, 5507 10.1039/c3cc41867g
21. Yang, D.-T.; Meng, Q.-Y.; Zhong, J.-J.; Xiang, M.; Liu, Q.; Wu, L.-Z. Eur. J. Org. Chem. 2013, 2013, 7528 10.1002/ejoc.201301105
22. Meng, Q.-Y.; Zhong, J.-J.; Liu, Q.; Gao, X.-W.; Zhang, H.-H.; Lei, T.; Li, Z.-J.; Feng, K.; Chen, B.; Tung, C.-H.; Wu, L.-Z. J. Am. Chem. Soc. 2013, 135, 19052 10.1021/ja408486v
23. Keshari, T.; Yadav, V. K.; Srivastava, V. P.; Yadav, L. D. S. Green Chem. 2014, 16, 3986 10.1039/C4GC00857J
24. Guy, R. G. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; John Wiley & Sons: New York, 1977; Part 2, p 819.
25. Nguyen, T.; Rubinstein, M.; Wakselman, C. J. Org. Chem. 1981, 46, 1938 10.1021/jo00322a047
26. Zhang, Z. H.; Liebeskind, L. S. Org. Lett. 2006, 8, 4331 10.1021/ol061741t
27. Riemschneider, R. J. Am. Chem. Soc. 1956, 78, 844 10.1021/ja01585a038
28. Lee, Y. T.; Choi, S. Y.; Chung, Y. K. Tetrahedron Lett. 2007, 48, 5673 and references cited therein. 10.1016/j.tetlet.2007.06.041
29. Patil, A. D.; Freyer, A. J.; Reichwein, R.; Carte, B.; Killmer, L. B.; Faucette, L.; Johnson, R. K.; Faulkner, D. J. Tetrahedron Lett. 1997, 38, 363 10.1016/S0040-4039(96)02304-0
30. Hill, H. A. O. In Chemistry and Biochemistry of Thiocyanic Acid and Its Derivatives; Newman, A. A., Ed.; Academic Press: London, 1975.
31. Dutta, S.; Abe, H.; Aoyagi, S.; Kibayashi, C.; Gates, K. S. J. Am. Chem. Soc. 2005, 127, 15004 10.1021/ja053735i
32. Pham, A. T.; Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Uchida, T.; Tanaka, J.-I.; Higa, T. Tetrahedron Lett. 1991, 32, 4843 10.1016/S0040-4039(00)93475-0
33. Zhu, D.; Chang, D.; Shi, L. Chem. Commun. 2015, 51, 7180 10.1039/C5CC00875A
34. Grant, M. S.; Snyder, H. R. J. Am. Chem. Soc. 1960, 82, 2742 10.1021/ja01496a023
35. Toste, F. D.; De Stefano, V.; Still, I. W. J. Synth. Commun. 1995, 25, 1277
36. Yadav, J. S.; Reddy, B. V. S.; Murali Krishna, B. B. Synthesis 2008, 2008, 3779 10.1055/s-0028-1083636
37. Bhalerao, D. S.; Akamanchi, K. G. Synlett 2007, 2007, 2952 10.1055/s-2007-992367
38. Fan, W.; Yang, Q.; Xu, F.; Li, P. J. Org. Chem. 2014, 79, 10588 10.1021/jo5015799
39. Enguehard-Gueiffier, C.; Gueiffier, A. Mini-Rev. Med. Chem. 2007, 7, 888 10.2174/138955707781662645
40. Stasyuk, A. J.; Banasiewicz, M.; Cyrański, M. K.; Gryko, D. T. J. Org. Chem. 2012, 77, 5552 10.1021/jo300643w
41. Shao, N.; Pang, G.-X.; Yan, C.- X.; Shi, G.-F.; Cheng, Y. J. Org. Chem. 2011, 76, 7458 10.1021/jo201273p
42. Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015, 51, 1555 10.1039/C4CC08495K
43. Pericherla, K.; Kaswan, P.; Pandey, K.; Kumar, A. Synthesis 2015, 47, 887 10.1055/s-0034-1380182
44. Koubachi, J.; El Kazzouli, S.; Bousmina, M.; Guillaumet, G. Eur. J. Org. Chem. 2014, 2014, 5119 10.1002/ejoc.201400065
45. He, C.; Hao, J.; Xu, H.; Mo, Y.; Liu, H.; Han, J.; Lei, A. Chem. Commun. 2012, 48, 11073 10.1039/c2cc35927h
46. Wang, H.; Wang, Y.; Liang, D.; Liu, L.; Zhang, J.; Zhu, Q. Angew. Chem., Int. Ed. 2011, 50, 5678 10.1002/anie.201100362
47. Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743 10.1002/anie.200907291
48. Zeng, J.; Tan, Y. J.; Leow, M. L.; Liu, X.-W. Org. Lett. 2012, 14, 4386 10.1021/ol301858j
49. Ravi, C.; Mohan, D. C.; Adimurthy, S. Org. Lett. 2014, 16, 2978 10.1021/ol501117z
50. Cao, H.; Liu, X.; Zhao, L.; Cen, J.; Lin, J.; Zhu, Q.; Fu, M. Org. Lett. 2014, 16, 146 10.1021/ol4031414
51. Yan, R.-L.; Yan, H.; Ma, C.; Ren, Z.-Y.; Gao, X.-A.; Huang, G.-S.; Liang, Y.-M. J. Org. Chem. 2012, 77, 2024 10.1021/jo202447p
52. Mishra, S.; Monir, K.; Mitra, S.; Hajra, A. Org. Lett. 2014, 16, 6084 10.1021/ol5028893
53. Monir, K.; Bagdi, A. K.; Ghosh, M.; Hajra, A. Org. Lett. 2014, 16, 4630 10.1021/ol502218u
54. Monir, K.; Bagdi, A. K.; Mishra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2014, 356, 1105 10.1002/adsc.201300900
55. Bagdi, A. K.; Rahman, M.; Santra, S.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1741 10.1002/adsc.201300298
56. Santra, S.; Bagdi, A. K.; Majee, A.; Hajra, A. Adv. Synth. Catal. 2013, 355, 1065 10.1002/adsc.201201112
57. Monir, K.; Bagdi, A. K.; Ghosh, M.; Hajra, A. J. Org. Chem. 2015, 80, 1332 10.1021/jo502928e
58. Ghosh, M.; Naskar, A.; Mitra, S.; Hajra, A. Eur. J. Org. Chem. 2015, 2015, 715 10.1002/ejoc.201403372
59. Bagdi, A. K.; Mitra, S.; Ghosh, M.; Hajra, A. Org. Biomol. Chem. 2015, 13, 3314 10.1039/C5OB00033E
60. Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.-C.; Witvrouw, M.; Balzarini, J.; De Clercq, E.; Chapat, J.-P. J. Med. Chem. 1998, 41, 5108 10.1021/jm981051y
61. Véron, J.-B.; Allouchi, H.; Enguehard-Gueiffier, C.; Snoeck, R.; Andrei, G.; De Clercq, E.; Gueiffier, A. Bioorg. Med. Chem. 2008, 16, 9536 10.1016/j.bmc.2008.09.027
62. Matheis, C.; Wang, M.; Krause, T.; Gooßen, L. J. Synlett 2015, 26, 1628 10.1055/s-0034-1378702
63. Wang, Q.; Qi, Z.; Xie, F.; Li, X. Adv. Synth. Catal. 2015, 357, 355 10.1002/adsc.201400717