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Volumn 72, Issue 4, 2007, Pages 1241-1245

Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se-Se, or Te-Te bond by a copper catalyst

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; COPPER COMPOUNDS; ORGANIC ACIDS; SYNTHESIS (CHEMICAL);

EID: 33846975476     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062131+     Document Type: Article
Times cited : (311)

References (68)
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    • The method using Cu catalyst: (a) Suzuki, H.; Abe, H.; Osuka, A. Chem. Lett. 1980, 1363-1364.
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    • Chalcogenations of alkyl halides or alkenyl borane with dichalcogenide are known. See: a
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    • A reaction of disulfide with RMgX or RLi can also give a corresponding monosulfide. But, this case cannot use one sulfide group on disulfide. See: Negishi, E, Ed, Wiley: New York
    • A reaction of disulfide with RMgX or RLi can also give a corresponding monosulfide. But, this case cannot use one sulfide group on disulfide. See: Negishi, E., Ed. Organometallics in Organic Synthesis; Wiley: New York, 1980.
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    • Transition metals can be inserted into dichalcogenide bonds: (a) Zanella, R.; Ros, R.; Graziani, M. Inorg. Chem. 1973, 12, 2736-2738.
    • Transition metals can be inserted into dichalcogenide bonds: (a) Zanella, R.; Ros, R.; Graziani, M. Inorg. Chem. 1973, 12, 2736-2738.
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    • In transition metal-catalyzed organic reactions using organoboronic acids, water has been added: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
    • In transition metal-catalyzed organic reactions using organoboronic acids, water has been added: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
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    • 3 as a ligand were employed, the yields were 58 and 4%, respectively.
    • 3 as a ligand were employed, the yields were 58 and 4%, respectively.
  • 57
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    • Other salts (KI and LiI) also gave the same results (63 and 68%, respectively).
    • Other salts (KI and LiI) also gave the same results (63 and 68%, respectively).
  • 62
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    • A disulfide bond can be cleaved by Cu(I)X: (a) Kadooka, M. M.; Warner, L. G.; Seff, K. J. Am. Chem. Soc. 1976, 98, 7569-7578.
    • A disulfide bond can be cleaved by Cu(I)X: (a) Kadooka, M. M.; Warner, L. G.; Seff, K. J. Am. Chem. Soc. 1976, 98, 7569-7578.
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    • It is well known that a transition metal can cleave a disulfide bond: (a) Bewick, A.; Mellor, J. M.; Milano, D.; Owton, W. M. J. Chem. Soc., Perkin Trans, I 1985, 1045-1048.
    • It is well known that a transition metal can cleave a disulfide bond: (a) Bewick, A.; Mellor, J. M.; Milano, D.; Owton, W. M. J. Chem. Soc., Perkin Trans, I 1985, 1045-1048.
  • 67
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    • Cu(I)-sulfide complex can be prepared by a reaction of disulfide with Cu(II)-salt in air: (a) Odani, A.; Maruyama, T.; Yamaguchi, O.; Fujiwara, T.; Tomita, K.-i. J. Chem. Soc., Chem. Commun. 1982, 646-647.
    • Cu(I)-sulfide complex can be prepared by a reaction of disulfide with Cu(II)-salt in air: (a) Odani, A.; Maruyama, T.; Yamaguchi, O.; Fujiwara, T.; Tomita, K.-i. J. Chem. Soc., Chem. Commun. 1982, 646-647.


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