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Volumn 45, Issue 29, 2004, Pages 5677-5679

Phosphine-free cationic rhodium(I) complex-catalyzed disulfide exchange reaction: Convenient synthesis of unsymmetrical disulfides

Author keywords

Disulfide; Disulfide exchange; Phosphine free; Rhodium

Indexed keywords

CATION; DISULFIDE; PHOSPHINE; RHODIUM COMPLEX; SOLVENT;

EID: 3042630882     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.092     Document Type: Article
Times cited : (68)

References (40)
  • 3
    • 0031797713 scopus 로고    scopus 로고
    • Recent examples of selective oxidative coupling of thiols to disulfides, see: metal oxidants:
    • Recent examples of selective oxidative coupling of thiols to disulfides, see: metal oxidants: Noureldin N.A., Caldwell M., Hendry J., Lee D.G. Synthesis. 1998;1587
    • (1998) Synthesis , pp. 1587
    • Noureldin, N.A.1    Caldwell, M.2    Hendry, J.3    Lee, D.G.4
  • 7
    • 0242321222 scopus 로고    scopus 로고
    • Synthesis of unsymmetrical disulfides by nucleophilic substitution of sulfenyl derivatives with thiols, see:
    • Synthesis of unsymmetrical disulfides by nucleophilic substitution of sulfenyl derivatives with thiols, see: Bao M., Shimizu M. Tetrahedron. 59:2003;9655
    • (2003) Tetrahedron , vol.59 , pp. 9655
    • Bao, M.1    Shimizu, M.2
  • 18
    • 0038333106 scopus 로고
    • Chem. Abstr. 1954, 48, 12699t
    • Leandri G., Tundo A. Ric. Sci. 23:1953;1646. Chem. Abstr. 1954, 48, 12699t
    • (1953) Ric. Sci. , vol.23 , pp. 1646
    • Leandri, G.1    Tundo, A.2
  • 25
    • 0000658944 scopus 로고
    • Sanger F. Nature. 171:1953;1025
    • (1953) Nature , vol.171 , pp. 1025
    • Sanger, F.1
  • 31
    • 0034251445 scopus 로고    scopus 로고
    • Transition metal-catalyzed cleavage of disulfide bond, see:
    • Transition metal-catalyzed cleavage of disulfide bond, see: Kondo T., Mitsudo T. Chem. Rev. 100:2000;3205
    • (2000) Chem. Rev. , vol.100 , pp. 3205
    • Kondo, T.1    Mitsudo, T.2
  • 33
    • 3042627431 scopus 로고    scopus 로고
    • note
    • 2 followed by hydrogenation (1 atm, rt, 0.5 h)
  • 35
    • 0033538289 scopus 로고    scopus 로고
    • First report for the dehydrogenation of benzenethiol to diphenyl disulfide under inert atmosphere, see:
    • First report for the dehydrogenation of benzenethiol to diphenyl disulfide under inert atmosphere, see: Ogawa A., Ikeda T., Kimura K., Hirao T. J. Am. Chem. Soc. 121:1999;5108
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5108
    • Ogawa, A.1    Ikeda, T.2    Kimura, K.3    Hirao, T.4
  • 36
    • 3042534821 scopus 로고    scopus 로고
    • note
    • The highest yield of disulfides was obtained at 4°C for 1 h (Eq. 1), but longer reaction time (16 h) at 4°C decreased the yield of disulfides and thiols were regenerated. This result indicates that this cationic rhodium(I)-catalyzed dehydrogenation reaction is reversible process. See Ref. 10
  • 37
    • 0038671666 scopus 로고
    • Disulfide-thiol exchange reaction, see:
    • Disulfide-thiol exchange reaction, see: Dalman G., McDermed J., Gorin G. J. Org. Chem. 29:1964;1480
    • (1964) J. Org. Chem. , vol.29 , pp. 1480
    • Dalman, G.1    McDermed, J.2    Gorin, G.3
  • 38
    • 3042578756 scopus 로고    scopus 로고
    • note
    • 3P/trifluoromethanesulfonic acid combination catalyst, see: Ref. 7
  • 39
    • 3042617846 scopus 로고    scopus 로고
    • note
    • 2, 80°C, 0.5 h) to give corresponding selenosulfide in 43% yield.
  • 40
    • 3042525192 scopus 로고    scopus 로고
    • note
    • 4 (12.2 mg, 0.030 mmol). The resulting solution was kept at 25°C for 1.5 h under air. The solution was concentrated and purified by silica gel chromatography (hexane/EtOAc = 20:1), which furnished n-butyl p-methoxyphenyl disulfide (370.8 mg, 1.62 mmol, 81%)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.