A highly efficient and widely functional-group-tolerant catalyst system for copper(I)-catalyzed S-arylation of thiols with aryl halides

Tetrahedron

Volumn 65, Issue 47, 2009, Pages 9737-9741

  Feng, Yang ^a   Wang, Huifeng ^a   Sun, Fangfang ^a   Li, Yaming ^a   Fu, Xinmei ^a   Jin, Kun ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; CARBON; CHLORIDE; CUPROUS ION; HALIDE; IODIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINOLINE DERIVATIVE; SULFUR; THIOL DERIVATIVE; THIOPHENOL;

ARTICLE; ARYLATION; CATALYST; CHEMICAL BOND; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 70349976432     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.085     Document Type: Article

References (48)

1. Kaldor S.W., Kalish V.J., Davies II J.F., Shetty B.V., Fritz J.E., Appelt K., Burgess J.A., Campanale K.M., Chirgadze N.Y., Clawson D.K., Dressman B.A., Hatch S.D., Khalil D.A., Kosa M.B., Lubbehusen P.P., Muesing M.A., Patick A.K., Reich S.H., Su K.S., and Tatlock J.H. J. Med. Chem. 40 (1997) 3979-3985
2. Wieslander E., Engman L., Svensj E., Erlansson M., Johansson U., Linden M., Andersson C.-M., and Brattsand R. Biochem. Pharmacol. 55 (1998) 573-584
3. Liu L., Stelmach J.E., Natarajan S.R., Chen M.-H., Singh S.B., Schwartz C.D., Fitzgerald C.E., O'Keefe S.J., Zaller D.M., Schmatz D.M., and Doherty J.B. Bioorg. Med. Chem. Lett. 13 (2003) 3979-3982
4. Lindley J. Tetrahedron 40 (1984) 1433-1456
5. Bordwell F.G., and McKellin W.H. J. Am. Chem. Soc. 73 (1951) 2251-2253
6. Migita T., Shimizu T., Asami Y., Shiobara J., Kato Y., and Kosugi M. Bull. Chem. Soc. Jpn. 53 (1980) 1385-1389
7. Kosugi M., Ogata T., Terada M., Sano H., and Migita T. Bull. Chem. Soc. Jpn. 58 (1985) 3657-3658
8. Kondo T., and Mitsudo T.-A. Chem. Rev. 100 (2000) 3205-3220
9. Li G.Y. Angew. Chem., Int. Ed. 40 (2001) 1513-1516
10. Murata M., and Buchwald S.L. Tetrahedron 60 (2004) 7397-7403
11. Fernández-Rodríguez M.A., Shen Q., and Hartwig J.F. Chem.-Eur. J. 12 (2006) 7782-7796
12. Fernandez-Rodríguez M.A., Shen Q., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 2180-2181
13. Itoh T., and Mase T. Org. Lett. 6 (2004) 4587-4590
14. Zhang Y., Ngeow K.N., and Ying J.Y. Org. Lett. 9 (2007) 3495-3499
15. Jammi S., Barua P., Rout L., Saha P., and Punniyamurthy T. Tetrahedron Lett. 49 (2008) 1484-1487
16. Cao Y.Q., Zhang Z., Guo Y.X., and Wu G.Q. Synth. Commun. 9 (2008) 1325-1332
17. For reviews:
18. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400-5449
19. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337-2364
20. Wong Y.C., Jayanth T.T., and Cheng C.H. Org. Lett. 8 (2006) 5613-5616
21. Correa A., Carril M., and Bolm C. Angew. Chem., Int. Ed. 47 (2008) 2880-2883
22. Wu W.Y., Wang J.C., and Tsai F.Y. Green. Chem. 11 (2009) 326-329
23. Reddy V.P., Swapna K., Kumar A.V., and Rao K.R. J. Org. Chem. 74 (2009) 3189-3191
24. Reddy V.P., Kumar A.V., Swapna K., and Rao K.R. Org. Lett. 11 (2009) 1697-1700
25. Palomo C., Oiarbide M., Lopez R., and Gomez-Bengoa E. Tetrahedron Lett. 41 (2000) 1283-1286
26. Kwong F.Y., and Buchwald S.L. Org. Lett. 4 (2002) 3517-3520
27. Enguehard-Gueiffier C., Thery I., Gueiffier A., and Buchwald S.L. Tetrahedron 62 (2006) 6042-6049
28. Bates C.G., Gujadhur R.K., and Venkataraman D. Org. Lett. 4 (2002) 2803-2806
29. Deng W., Zou Y., Wang Y.F., Liu L., and Guo Q.X. Synlett (2004) 1254-1258
30. Zhu D., Xu L., Wu F., and Wan B. Tetrahedron Lett. 47 (2006) 5781-5784
31. Chen Y.-J., and Chen H.-H. Org. Lett. 8 (2006) 5609-5612
32. Verma A.K., Singh J., and Chaudhary R. Tetrahedron Lett. 48 (2007) 7199-7202
33. Carril M., SanMartin R., Dominguez E., and Tellitu I. Chem.-Eur. J. 13 (2007) 5100-5105
34. Herrero M.T., SanMartin R., and Dominguez E. Tetrahedron 65 (2009) 1500-1503
35. Lv X., and Bao W. J. Org. Chem. 72 (2007) 3863-3867
36. Xu H., Zhao X., Deng J., Fu Y., and Feng Y. Tetrahedron Lett. 50 (2009) 434-437
37. Zhang H., Cao W., and Ma D. Synth. Commun. 37 (2007) 25-35
38. Prasad D.J.C., Naidu A.B., and Sekar G. Tetrahedron Lett. 50 (2009) 1411-1415
39. Rout L., Sen T.K., and Punniyamurthy T. Angew. Chem., Int. Ed. 46 (2007) 5583-5586
40. Ranu B.C., Saha A., and Jana R. Adv. Synth. Catal. 349 (2007) 2690-2696
41. Sperotto E., van Klink G.P.M., de Vries J.G., and van Koten G. J. Org. Chem. 73 (2008) 5625-5628
42. Xu H.J., Zhao X.Y., Fu Y., and Feng Y.S. Synlett (2008) 3063-3067
43. Rout L., Saha P., Jammi S., and Punniyamurthy T. Eur. J. Org. Chem. (2008) 640-643
44. Buranaprasertsuk P., Chang J.W.W., Chavasiri W., and Chan P.W.H. Tetrahedron Lett. 49 (2008) 2023-2025
45. Wang H.F., Li Y.M., Sun F.F., Feng Y., Jin K., and Wang X.N. J. Org. Chem. 73 (2008) 8639-8642
46. Bates R.B., and Janda K.D. J. Org. Chem. 47 (1982) 4374-4376
47. Shi L., Wang M., Fan C.A., Zhang F.M., and Tu Y.Q. Org. Lett. 5 (2003) 3515-3517
48. Zhang S.L., Liu L., Fu Y., and Guo Q.X. Organometallics 26 (2007) 4546-4554