Addition reaction of dialkyl disulfides to terminal alkynes catalyzed by a rhodium complex and trifluoromethanesulfonic acid

Organic Letters

Volumn 3, Issue 5, 2001, Pages 763-764

  Arisawa, Mieko ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

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EID: 0001140859     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015521l     Document Type: Article

References (12)

1. Kuniyasu, H.; Ogawa, A.; Miyazaki, S.-I.; Ryu, I.; Kamhe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 4796. Ogawa, A.; Kuniyasu, H.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.
2. Kuniyasu, H.; Ogawa, A.; Miyazaki, S.-I.; Ryu, I.; Kamhe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 4796. Ogawa, A.; Kuniyasu, H.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.
3. Gareau, Y.; Orellana, A. Synlett 1997, 803.
4. Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1967, 32, 3837. Also see the followings for the addition of diselenides to alkynes. Ogawa, A.; Yokoyama, H.; Yokoyama, K.; Masawaki, T.; Kambe, N.; Sonoda, N. J. Org. Chem. 1991, 56, 5721. Back, T. G.; Krishna, M. V. J. Org. Chem. 1988, 53, 2533.
5. Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1967, 32, 3837. Also see the followings for the addition of diselenides to alkynes. Ogawa, A.; Yokoyama, H.; Yokoyama, K.; Masawaki, T.; Kambe, N.; Sonoda, N. J. Org. Chem. 1991, 56, 5721. Back, T. G.; Krishna, M. V. J. Org. Chem. 1988, 53, 2533.
6. Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1967, 32, 3837. Also see the followings for the addition of diselenides to alkynes. Ogawa, A.; Yokoyama, H.; Yokoyama, K.; Masawaki, T.; Kambe, N.; Sonoda, N. J. Org. Chem. 1991, 56, 5721. Back, T. G.; Krishna, M. V. J. Org. Chem. 1988, 53, 2533.
7. Tazaki, M.; Kumakura, M.; Nagahama, S.; Takagi, M. J. Chem. Soc., Chem. Commun. 1995, 1763.
8. Addition of phosphine to alkyne: Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Beckmann rearrangement: Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311.
9. Addition of phosphine to alkyne: Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Beckmann rearrangement: Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311.
10. Addition of phosphine to alkyne: Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Beckmann rearrangement: Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311.
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12. In a two-necked flask equipped with a reflux condenser were placed tetrakis(triphenylphosphine)hydriderhodium (3 mol %, 17.3 mg), tris(p-methoxyphenyl)phosphine (12 mol %, 21.1 mg), trifluoromethanesulfonic acid (3 mol %, 1.4 μL), 1-octyne (0.5 mmol, 73.8 μL), and dibutyl disulfide (0.5 mmol, 95.1 μL) in acetone (1.0 mL) under an argon atmosphere, and the solution was heated at reflux for 10 h. Then, the solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel giving (Z)-1,2-bis(butylthio)-1-octene (137 mg, 95%).