Rhodium-Catalyzed Regio- and Stereoselective 1-Seleno-2-thiolation of 1-Alkynes

Journal of Organic Chemistry

Volumn 68, Issue 23, 2003, Pages 8964-8967

  Arisawa, Mieko ^a   Kozuki, Yoshihiro ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVE ADDITIONS;

ADDITION REACTIONS; CATALYSIS; CATALYST ACTIVITY;

ORGANIC COMPOUNDS;

1 BUTYLSELENO 2 BUTYLTHIO 1 OCTENE; 1 SELENO 2 THIOL DERIVATIVE; 1,1' BIS(DIPHENYLPHOSPHINO)FERROCENE; 1,4 DIPHENYLPHOSPHINOBUTANE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; DIBUTYL DISELENIDE; DIBUTYL DISULFIDE; DISELENIDE DERIVATIVE; DISULFIDE; FERROCENE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM; RHODIUM COMPLEX; SELENIUM DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CONCENTRATION RESPONSE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 0242576755     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034990t     Document Type: Article

References (14)

1. See the following examples for the synthesis of such com-pounds: (a) Back, T. G.; Bethell, R. J.; Parvez, M.; Wehrli, D. J. Org. Chem. 1998, 63, 7908.
2. (b) Hibino, M.; Koike, T.; Yoshimatsu, M. J. Org. Chem. 2002, 67, 1078.
3. (c) Billard, T.; Langlois, B. R. Tetrahedron 1999, 55, 8065.
4. (a) Ogawa, A.; Obayashi, R.; Ine, H.; Tsuboi, Y.; Sonoda, N.; Hirao, T. J. Org. Chem. 1998, 63, 881.
5. (b) Ogawa, A.; Hirao, T. Rev. Heteroat. Chem. 1998, 18, 1.
6. Potapov, V. A.; Amosova, S. V.; Zhnikin, A. R.; Sedunova, O. V.; Starkova, A. A. Sulfur Lett. 2001, 24, 251.
7. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763.
8. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M. Adv. Synth. Catal. 2003, 345, 560.
9. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2003, 125, 6624. It was later found that trifluoromethanesulfonic acid was not essential for the exchange of a disulfide and a diselenide.
10. Gulliver, D. J.; Hope, E. G.; Levason, W.; Murray, S. G.; Potter, D. M.; Marshall, G. L. J. Chem. Soc., Perkin Trans. 2 1984, 429.
11. Kuniyasu, H.; Ogawa, A.; Miyazaki, S.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796.
12. For example: Ikeda, T.; Mizobe, Y.; Hidai, M. Organometallics, 2001, 20, 4441.
13. Cristau, H. J.; Chabaud, B.; Labaudiniere, R.; Christol, H. J. Org. Chem. 1986, 51, 875.
14. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D. Montanucci, M. Tetrahedron Lett. 1984, 25, 4975.