Activation of aryl thiocyanates followed by aryne insertion: Access to 1,2-thiobenzonitriles

Organic Letters

Volumn 17, Issue 7, 2015, Pages 1716-1719

  Pawliczek, Martin ^a,b   Garve, Lennart K B ^a   Werz, Daniel B ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE; PALLADIUM; SULFUR; THIOCYANIC ACID DERIVATIVE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; MOLECULAR STRUCTURE; NITRILES; PALLADIUM; SULFUR; THIOCYANATES;

EID: 84926454447     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00494     Document Type: Article

References (49)

1. Bagley, M. C.; Davis, T.; Dix, M. C.; Fusillo, V.; Pigeaux, M.; Rokicki, M. J.; Kipling, D. J. Org. Chem. 2009, 74, 8336
2. De Martino, G.; Edler, M. C.; La Regina, G.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947
3. Popoff, I. C.; Engle, A. R.; Whitaker, R. L.; Shinghal, G. H. J. Med. Chem. 1971, 14, 1166
4. Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596
5. Yang, H.; Li, Y.; Jiang, M.; Wang, J.; Fu, H. Chem.-Eur. J. 2011, 17, 5652
6. Anbarasan, P.; Neumann, H.; Beller, M. Chem. Commun. 2011, 47, 3233
7. Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 454
8. Li, Y.; Li, X.; Wang, H.; Chen, T.; Xie, Y. Synthesis 2010, 3602
9. Xu, H.-J.; Zhao, X.-Y.; Deng, J.; Feng, Y.-S. Tetrahedron Lett. 2009, 50, 434
10. Huang, F.; Batey, R. A. Tetrahedron 2007, 63, 7667
11. Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. Chem.-Eur. J. 2006, 12, 7782
12. Yang, Y.; Chen, Z.; Rao, Y. Chem. Commun. 2014, 50, 15037
13. Qui, J.-K.; Hao, W.-J.; Wang, D.-C.; Wei, P.; Sun, J.; Jiang, B.; Tu, S.-J. Chem. Commun. 2014, 50, 14782
14. Yang, F.-L.; Tian, S.-K. Angew. Chem., Int. Ed. 2013, 52, 4929
15. Umiersky, N.; Manolikakes, G. Org. Lett. 2013, 15, 188
16. Liang, S.; Zhang, R.; Xi, L.; Chen, S.; Yu, X. J. Org, Chem. 2013, 78, 5652
17. Miyazaki, Y.; Ohta, N.; Semba, K.; Nakao, Y. J. Am. Chem. Soc. 2014, 136, 3732
18. Pan, Z.; Pound, S. M.; Rondla, N. R.; Douglas, C. J. Angew. Chem., Int. Ed. 2014, 53, 5170
19. Koester, D. C.; Kobayashi, M.; Werz, D. B.; Nakao, Y. J. Am. Chem. Soc. 2012, 134, 6544
20. Ozaki, T.; Nomoto, A.; Kamiya, I.; Kawakami, J.-I.; Ogawa, A. Bull. Chem. Soc. Jpn. 2011, 84, 155
21. Zheng, W.; Ariafard, A.; Lin, Z. Organometallics 2008, 27, 246
22. Tak, Y.; Choi, S. Y.; Chung, Y. K. Tetrahedron Lett. 2007, 48, 5673
23. Kamiya, I.; Kawakami, J.-I.; Yano, S.; Nomoto, A.; Ogawa, A. Organometallics 2006, 25, 3562
24. Rao, B.; Zeng, X. Org. Lett. 2014, 16, 314
25. Gracía-López, J.-A.; Greaney, M. F. Org. Lett. 2014, 16, 2338
26. Luo, K.; Meng, L.; Zhang, Y.; Zhang, X.; Wang, L. Adv. Synth. Catal. 2013, 355, 765
27. Liu, X.; Wang, X.; Li, Q.; Kozar, M. P.; Melendez, V.; ONeil, M. T.; Lin, A. J. J. Med. Chem. 2011, 54, 4523
28. Devan, B.; Rajagopalan, K. Synth. Commun. 1994, 24, 1691
29. Melzig, L.; Rauhut, C. B.; Naredi-Rainer, N.; Knochel, P. Chem.-Eur. J. 2011, 17, 5362
30. Werz, D. B.; Fischer, F. R.; Kornmayer, S. C.; Rominger, R.; Gleiter, R. J. Org. Chem. 2008, 73, 8021
31. Werz, D. B.; Gleiter, R.; Rominger, F. J. Org. Chem. 2004, 69, 2945
32. Werz, D. B.; Gleiter, R. J. Org. Chem. 2003, 68, 9400
33. Schulte, J. H.; Werz, D. B.; Rominger, F.; Gleiter, R. Org. Biomol. Chem. 2003, 1, 2788
34. Rausch, B. J.; Werz, D. B.; Rittinger, S.; Gleiter, R.; Oeser, T.; Rominger, F. J. Chem. Soc., Perkin Trans. 2 2002, 72
35. Benisch, C.; Bethke, S.; Gleiter, R.; Oeser, T.; Pritzkow, H.; Rominger, F. Eur. J. Org. Chem. 2000, 2479
36. Toste, D. F.; Still, I. W. J. Tetrahedron Lett. 1995, 36, 4361
37. Garve, L. K. B.; Werz, D. B. Org. Lett. 2015, 17, 596
38. Dong, Y.; Liu, B.; Chen, P.; Liu, Q.; Wang, M. Angew. Chem., Int. Ed. 2014, 53, 3442
39. Ye, W.; Zhang, L.; Ni, C.; Rong, J.; Hu, J. Chem. Commun. 2014, 50, 10596
40. Lui, F.-L.; Chen, J.-R.; Zou, Y.-Q.; Wie, Q.; Xiao, W.-J. Org. Lett. 2014, 16, 3768
41. Bhunia, A.; Roy, T.; Pachfule, P.; Rajamohanan, P.; Biju, A. T. Angew. Chem., Int. Ed. 2013, 52, 10040
42. Dubrovskiy, A.; Larock, R. C. J. Org. Chem. 2012, 77, 11232
43. Kim, J.; Stoltz, B. M. Tetrahedron Lett. 2012, 53, 4994
44. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
45. Tadross, P. M.; Gilmore, C. D.; Bugga, P.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2010, 12, 1224
46. Ebner, D. C.; Tambar, U. K.; Stoltz, B. M. Org. Synth. 2009, 86, 161
47. Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5340
48. Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712
49. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412