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Volumn 6, Issue 1, 2004, Pages 107-110

Direct Copper(I) Iodide Dimethyl Sulfide Catalyzed Conjugate Addition of Alkenyl Groups from Vinylzirconocene Reagents

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; COPPER DERIVATIVE; DIMETHYL SULFIDE; IODINE DERIVATIVE; REAGENT; VINYL DERIVATIVE; ZIRCONOCENE;

EID: 0742321834     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036141y     Document Type: Article
Times cited : (25)

References (34)
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    • The CuI·DMS complex is unstable and loses rapidly DMS to form the more stable CuI·0.75DMS stoichiometry, as determined by elemental analysis. For a discussion on the stability of CuI·DMS complex, see: Eriksson, M.; Hjelmencrantz, A.; Nilsson, M.; Olsson, T. Tetrahedron 1995, 51, 12631-12644. See also: Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182-187. For CuI purified via its dimethyl sulfide complex, see: House, H. O.; Chu, C.-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem., 1975, 40, 1460-1469.
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    • The CuI·DMS complex is unstable and loses rapidly DMS to form the more stable CuI·0.75DMS stoichiometry, as determined by elemental analysis. For a discussion on the stability of CuI·DMS complex, see: Eriksson, M.; Hjelmencrantz, A.; Nilsson, M.; Olsson, T. Tetrahedron 1995, 51, 12631-12644. See also: Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182-187. For CuI purified via its dimethyl sulfide complex, see: House, H. O.; Chu, C.-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem., 1975, 40, 1460-1469.
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    • The CuI·DMS complex is unstable and loses rapidly DMS to form the more stable CuI·0.75DMS stoichiometry, as determined by elemental analysis. For a discussion on the stability of CuI·DMS complex, see: Eriksson, M.; Hjelmencrantz, A.; Nilsson, M.; Olsson, T. Tetrahedron 1995, 51, 12631-12644. See also: Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182-187. For CuI purified via its dimethyl sulfide complex, see: House, H. O.; Chu, C.-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem., 1975, 40, 1460-1469.
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    • note
    • 1H NMR data obtained from crude reaction mixtures.
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    • A few stable copper(III) species have been isolated, see: (a) Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633-1634. (b) Naumann D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem. 1993, 105, 1555-1556. (c) Naumann D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483. (d) Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
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    • A few stable copper(III) species have been isolated, see: (a) Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633-1634. (b) Naumann D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem. 1993, 105, 1555-1556. (c) Naumann D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483. (d) Eujen, R.; Hoge, B.; Brauer, D. J. J. Organomet. Chem. 1996, 519, 7-20.
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