Stereo-recognizing transformation of (E)-alkenyl halides into sulfides catalyzed by nickel(0) triethyl phosphite complex

Tetrahedron

Volumn 62, Issue 42, 2006, Pages 9981-9987

  Yatsumonji, Yasutaka ^a   Okada, Orie ^a   Tsubouchi, Akira ^a   Takeda, Takeshi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Cross coupling; Nickel(0) complexes; Sulfides; Thiols

Indexed keywords

ALKENYL GROUP; HALIDE; NICKEL COMPLEX; PHOSPHITE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; SULFIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL;

EID: 33748192036     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.001     Document Type: Article

References (64)

1. Gschwend H.W., and Rodriguez H.R. Org. React. 26 (1979) 32
2. Oshima K., Shimoji K., Takahashi H., Yamamoto H., and Nozaki H. J. Am. Chem. Soc. 95 (1973) 2694
3. Takeda T., Furukawa H., Fujimori M., Suzuki K., and Fujiwara T. Bull. Chem. Soc. Jpn. 57 (1984) 1863
4. Trost B.M., and Lavoie A.C. J. Am. Chem. Soc. 105 (1983) 5075
5. Miller R.D., and Hassig R. Tetrahedron Lett. 26 (1985) 2395
6. Takeda T., Fujii T., Morita K., and Fujiwara T. Chem. Lett. 15 (1986) 1311
7. Narasaka K., Hayashi Y., Shimadzu H., and Niihata S. J. Am. Chem. Soc. 114 (1992) 8869
8. Takeda T., and Fujiwara T. Synlett (1996) 481
9. Cookson R.C., and Persons P.J. J. Chem. Soc., Chem. Commun. (1976) 990
10. Takeda T., and Fujiwara T. Chem. Lett. 11 (1982) 1113
11. Magnus P., and Quagliato D. J. Org. Chem. 50 (1985) 1621
12. Morris T.H., Smith E.H., and Walsh R. J. Chem. Soc., Chem. Commun. (1987) 964
13. Mizuno H., Domon K., Masuya K., Tanino K., and Kuwajima I. J. Org. Chem. 64 (1999) 2648
14. Masuya K., Domon K., Tanino K., and Kuwajima I. Synlett (1996) 157
15. Murahashi S., Yamamura M., Yanagisawa K., Mita N., and Kondo K. J. Org. Chem. 44 (1979) 2408
16. Foa M., Santi R., and Garavaglia F. J. Organomet. Chem. 206 (1981) C29
17. Carpita A., Rossi R., and Scamuzzi B. Tetrahedron Lett. 30 (1989) 2699
18. Martínez A.G., Barcina J.O., de Fresno Cerezo A., and Subramanian L.R. Synlett (1994) 561
19. Baranano D., Mann G., and Hartwig J.F. Curr. Org. Chem. 1 (1997) 287
20. Moreau X., and Campagne J. J. Organomet. Chem. 687 (2003) 322
21. Rane A.M., Miranda E.I., and Soderquist J.A. Tetrahedron Lett. 35 (1994) 3225
22. Li G.Y. J. Org. Chem. 67 (2002) 3643
23. Commercon A., Normant J., and Villieras J. J. Organomet. Chem. 93 (1975) 415
24. Ogawa T., Hayami K., and Suzuki H. Chem. Lett. 18 (1989) 769
25. Bates C.G., Saejueng P., Doherty M.Q., and Venkataraman D. Org. Lett. 6 (2004) 5005
26. Cristau H.J., Chabaud B., Labaudiniere R., and Christol H. J. Org. Chem. 51 (1986) 875
27. Ogata A., Nemoto M., Arai K., Kobayashi K., Tsubouchi A., and Takeda T. Eur. J. Org. Chem. (2006) 878
28. Vinal R.S., and Reynald L.T. Inorg. Chem. 3 (1964) 1062
29. Fujiwara T., Yanagihara H., Yamada T., and Takeda T. Chem. Lett. 15 (1985) 1629
30. Takeda T., Kanamori F., Masuda M., and Fujiwara T. Tetrahedron Lett. 32 (1991) 5567
31. When a similar oxidation was performed after the Ni(0) catalyzed formation of alkenyl sulfide 3a without light shielding, both E- and Z-isomers of the corresponding sulfoxide 5a were obtained (E/Z=95:5) in 90% yield.
32. Lin B.-L., Liu L., Fu Y., Luo S.-W., Chan Q., and Guo Q.-X. Organometallics 23 (2004) 2114
33. Kosugi M., Shimizu T., and Migita T. Chem. Lett. 16 (1978) 13
34. Migita T., Shimizu T., Asami Y., Shiobara J., Kato Y., and Kosugi M. Bull. Chem. Soc. Jpn. 53 (1980) 1385
35. Kosugi M., Ogata T., Terada M., Sano H., and Migita T. Bull. Chem. Soc. Jpn. 58 (1985) 3657
36. Ciattini P.G., Morera E., and Ortar G. Tetrahedron Lett. 36 (1995) 4133
37. Baranano D., and Hartwig J.F. J. Am. Chem. Soc. 117 (1995) 2937
38. Mann G., Baranano D., Hartwig J.F., Rheingold A.L., and Guzei I.A. J. Am. Chem. Soc. 120 (1998) 9205
39. Zheng N., McWilliams J.C., Fleitz F.J., Armstrong III J.D., and Volante R.P. J. Org. Chem. 63 (1998) 9606
40. Hartwig J.F. Acc. Chem. Res. 31 (1998) 852
41. Li G.Y., Zheng G., and Noonan A.F. J. Org. Chem. 66 (2001) 8677
42. Li G.Y. Angew. Chem., Int. Ed. 40 (2001) 1513
43. Wolf C., and Lerebours R. J. Org. Chem. 68 (2003) 7077
44. Itoh T., and Mase T. Org. Lett. 6 (2004) 4587
45. Murata M., and Buchwald S.L. Tetrahedron 60 (2004) 7397
46. Fernández-Rodriguez M.A., Shen Q., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 2180
47. Suzuki H., Abe H., and Osuka A. Chem. Lett. 9 (1980) 1363
48. Hickman R.J.S., Christie B.J., Guy R.W., and White T.J. Aust. J. Chem. 38 (1985) 899
49. Palomo C., Oiarbide M., López R., and Gómez-Bengoa E. Tetrahedron Lett. 41 (2000) 1283
50. Bates C.G., Gujadhur R.K., and Venkataraman D. Org. Lett. 4 (2002) 2803
51. Kwong F.Y., and Buchwald S.L. Org. Lett. 4 (2002) 3517
52. Wu Y.-J., and He H. Synthesis (2003) 1789
53. Nauš P., Lešetický L., Smrćek S., Tišlerová I., and Štícha M. Synlett (2003) 2117
54. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
55. Deng W., Zou Y., Wang Y.-F., Liu L., and Guo Q.-X. Synlett (2004) 1254
56. Lohman S., Andrews S.P., Burke B.J., Smith M.D., Attfield J.P., Tanaka H., Kaneko K., and Ley S.V. Synlett (2005) 1291
57. Varala R., Ramu E., Alam M.M., and Adapa S.R. Chem. Lett. 33 (2004) 1614
58. Cristau H.J., Chabaud B., Chêne A., and Christol H. Synthesis (1981) 892
59. Takagi K. Chem. Lett. 16 (1987) 2221
60. Tiecco M., Testaferri L., Tingoli M., Chianelli D., and Montanucci M. J. Org. Chem. 48 (1983) 4795
61. Ogawa A., Ikeda T., Kimura K., and Hirao T. J. Am. Chem. Soc. 121 (1999) 5108
62. Fleming I., and Ramarao C. Org. Biomol. Chem. 2 (2004) 1504
63. Daub G.H. J. Org. Chem. 41 (1976) 883
64. Wnuk S.F., Garcia Jr. P.I., and Wang Z. Org. Lett. 6 (2004) 2047