A novel copper(II)/Tin(II) reagent for aqueous carbonyl allylation: In situ diagnostics of reactive organometallics in water

Organometallics

Volumn 16, Issue 22, 1997, Pages 4796-4799

  Kundu, Abhijit ^a   Prabhakar, Sripadi ^a   Vairamani, M ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000419672     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9704096     Document Type: Article

References (39)

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6. For aqueous allylation using tin salts see: (a) Masuyama, Y.; Takahara, T. P.; Kurusu, Y. Tetrahedron Lett. 1989, 30, 3437. (b) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. (c) Sati, M.; Sinou, D. Tetrahedron Lett. 1991, 32, 2025. (d) Uneyama, K.; Ueda, K.; Torii, S. Chem. Lett. 1986, 1201. (e) Masuyama, Y.; Kishida, M.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1995, 1405.
7. For aqueous allylation using tin salts see: (a) Masuyama, Y.; Takahara, T. P.; Kurusu, Y. Tetrahedron Lett. 1989, 30, 3437. (b) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. (c) Sati, M.; Sinou, D. Tetrahedron Lett. 1991, 32, 2025. (d) Uneyama, K.; Ueda, K.; Torii, S. Chem. Lett. 1986, 1201. (e) Masuyama, Y.; Kishida, M.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1995, 1405.
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27. For the influence of solvent on the regio- and diastereoselectivity in allylation see: Masuyama, Y. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, p 255.
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31. 1H) coupling.
32. 6 (Jardine, F. H. Adv. Inorg. Chem. Radiochem. 1975, 17, 115), metastable solutions of aquocopper(I) complexes can be generated in acidic aqueous media by reducing Cu(II) salts with Eu(II), Cr(II), V(II), or Sn(II) halides (Nunes, T. L. Inorg. Chem. 1970, 9, 1325).
33. 6 (Jardine, F. H. Adv. Inorg. Chem. Radiochem. 1975, 17, 115), metastable solutions of aquocopper(I) complexes can be generated in acidic aqueous media by reducing Cu(II) salts with Eu(II), Cr(II), V(II), or Sn(II) halides (Nunes, T. L. Inorg. Chem. 1970, 9, 1325).
34. (b) For an olefin-copper(I) interaction see: Quinn, H. W.; Tsai, J. H. Adv. Inorg. Chem. Radiochem. 1969, 12, 327. Munakata, M.; Kitagawa, S.; Kosome, S.; Asahara, A. Inorg. Chem. 1986, 25, 2622.
35. (b) For an olefin-copper(I) interaction see: Quinn, H. W.; Tsai, J. H. Adv. Inorg. Chem. Radiochem. 1969, 12, 327. Munakata, M.; Kitagawa, S.; Kosome, S.; Asahara, A. Inorg. Chem. 1986, 25, 2622.
36. (c) For a discussion on allyl-copper(I) interaction see: Baruah, J. B.; Samuelson, A. G. New J. Chem. 1994, 18, 961.
37. CV in aqueous media did not show reversibility, indicating the instability of the redox species in the absence of coordinative stabilization.
38. For organostannanes, EIMS is a more effective probe than FABMS: Harrison, P. G. Chemistry of Tin; Blackie: London, 1989; p 105.
39. The exclusive formation of tribenzyltin chloride from the reaction of benzyl chloride and tin metal in water was reported earlier: Sisido, K.; Takeda, Y.; Kinugawa, Z. J. Am. Chem. Soc. 1961, 83, 538.