Chelate-assisted direct selenation of aryl C-H bonds with diselenides catalyzed by palladium

Organic Letters

Volumn 16, Issue 18, 2014, Pages 4920-4923

  Iwasaki, Masayuki ^a   Tsuchiya, Yuta ^a   Nakajima, Kiyohiko ^b   Nishihara, Yasushi ^a,c  

^a OKAYAMA UNIVERSITY   (Japan)

^b AICHI UNIVERSITY OF EDUCATION   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84916201916     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502439m     Document Type: Article

References (55)

1. For recent reviews, see: (a) Mugesh, G.; Du Mont, W.-W.; Sies, H. Chem. Rev. 2001, 101, 2125.
2. (b) Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Chem. Rev. 2004, 104, 6255.
3. (a) Woods, J. A.; Hadfield, J. A.; McGrown, A. T.; Fox, B. W. Bioorg. Med. Chem. 1993, 1, 333.
4. (b) Engman, L.; Stern, D.; Frisell, H.; Vessman, K.; Berglund, M.; Ek, B.; Andersson, C.-M. Bioorg. Med. Chem. 1995, 3, 1255.
5. (a) Okamoto, Y. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U. K., 1986.
6. (b) Ando, T.; Kwon, T. S.; Kitagawa, A.; Tanemura, T.; Kondo, S.; Kunisada, H.; Yuki, Y. Macromol. Chem. Phys. 1996, 197, 2803.
7. Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
8. (a) Taniguchi, N. J. Org. Chem. 2007, 72, 1241.
9. (b) Ren, K.; Wang, M.; Wang, L. Org. Biomol. Chem. 2009, 7, 4858.
10. (c) Ricordi, V. G.; Freitas, C. S.; Perin, G.; Lenardao, E. J.; Jacob, R. G.; Savegnago, L.; Alves, D. Green Chem. 2012, 14, 1030.
11. (a) Nishiyama, Y.; Tokunaga, K.; Sonoda, N. Org. Lett. 1999, 1, 1725.
12. (b) Millois, C.; Diaz, P. Org. Lett. 2000, 2, 1705.
13. (c) Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii, P. V.; Khrustalev, V. N. Chem. Lett. 2010, 39, 720.
14. (d) Zhao, H.; Hao, W.; Xi, Z.; Cai, M. New J. Chem. 2011, 35, 2661.
15. (a) Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
16. (b) Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
17. (c) Kumar, S.; Engman, L. J. Org. Chem. 2006, 71, 5400.
18. (d) Fukuzawa, S.; Tanihara, D.; Kikuchi, S. Synlett 2006, 2145.
19. (e) Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Org. Lett. 2009, 11, 951.
20. (f) Chatterjee, T.; Ranu, B. C. J. Org. Chem. 2013, 78, 7145.
21. (a) Suzuki, H.; Abe, H.; Osuka, A. Chem. Lett. 1981, 151.
22. (b) Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Christol, H. Organometallics 1985, 4, 657.
23. (c) Evers, M. J.; Christiaens, L. E.; Renson, M. J. J. Org. Chem. 1986, 51, 5196.
24. (d) Taniguchi, N. Synlett 2005, 1687.
25. Another type of the C-Se bond formation has been reported, see: Zhang, W.-X.; Wang, Z.; Xi, Z. Angew. Chem., Int. Ed. 2011, 50, 8122.
26. For recent reviews on catalytic direct aryl C-X (B, N, O, Si, and halogen) bond formation, see: (a) Sehnal, P.; Taylor, R J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824.
27. (b) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
28. (c) Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788.
29. (d) Vedernikov, A N. Acc. Chem. Res. 2012, 45, 803.
30. (e) Powers, D. C; Ritter, T. Acc. Chem. Res. 2012, 45, 840.
31. (f) Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864.
32. (g) Neufeldt, S. R; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936.
33. For phosphonation, see: (h) Li, C; Yano, T.; Ishida, N; Murakami, M. Angew. Chem., Int. Ed. 2013, 52, 9801.
34. For stannylation, see: (i) Doster, M. E.; Hatnean, J. A; Jeftic, T.; Modi, S.; Johnson, S. A J. Am. Chem. Soc. 2010, 132, 11923.
35. For germanylation, see: (j) Kanyiva, K. S.; Kuninobu, Y.; Kanai, M. Org. Lett. 2014, 16, 1968.
36. Hegedus, L. L.; McCabe, R W. Catalyst Poisoning; Marcel Dekker: New York, 1984.
37. (a) Zhang, S.; Qian, P.; Zhang, M.; Hu, M.; Cheng, J. J. Org. Chem. 2010, 75, 6732.
38. (b) Shibahara, F.; Kanai, T.; Yamaguchi, E.; Kamei, A.; Yamauchi, T.; Murai, T. Chem.-Asian J. 2014, 9, 237.
39. Iwasaki, M.; Iyanaga, M.; Tsuchiya, Y.; Nishimura, Y.; Li, W.; Li, Z.; Nishihara, Y. Chem.-Eur. J. 2014, 20, 2459.
40. (a) Tran, L. D.; Popov, I.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 18237.
41. (b) Yang, Y.; Hou, W.; Qin, L.; Du, J.; Feng, H.; Zhou, B.; Li, Y. Chem.-Eur. J. 2014, 20, 416.
42. (c) Xu, C; Shen, Q. Org. Lett. 2014, 16, 2046.
43. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
44. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726 and references therein.
45. Crystallographic data for the structure of 3a have been deposited with The Cambridge Crystallographic Data Centre as the deposition number CCDC-1019170. This data can be obtained free of charge from an application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0) 1223 336033 or www.ccdc.cam.ac.uk/data-request/cif.
46. For the palladium-catalyzed direct arylation of benzamides with aryl halides, see: (a) Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655.
47. (b) Shabashov, D.; Daugulis, O. Org. Lett. 2006, 8, 4947.
48. (c) Shabashov, D.; Molina Maldonado, J. R; Daugulis, O. J. Org. Chem. 2008, 73, 7818.
49. (d) Wang, G.-W.; Yuan, T.-T.; Li, D.-D. Angew. Chem., Int. Ed. 2011, 50, 1380.
50. (e) Peron, F.; Fossey, C.; Cailly, T.; Fabis, F. Org. Lett. 2012, 14, 1827.
51. (f) Li, D.-D.; Yuan, T.-T.; Wang, G.-W. J. Org. Chem. 2012, 77, 3341.
52. (g) Msal Castro, L. C.; Chatani, N. Chem.-Eur. J. 2014, 20, 4548.
53. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066.
54. Canty, A J.; Jin, H.; Skelton, B. W.; White, A. H. Inorg. Chem. 1998, 37, 3975.
55. Brennan, N. K; Donnelly, D. J.; Detty, M. R J. Org. Chem. 2003, 68, 3344.