Pinacol coupling of aromatic aldehydes catalysed by a titanocene complex: a transition metal catalysed radical reaction

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Andreas Gansäuer


Abstract

A trinuclear complex derived from titanocene chloride and magnesium bromide is an efficient catalyst for the pinacol coupling of aromatic aldehydes; the 1,2-diols are obtained with good diastereoselectivity and a wide variety of sensitive functional groups are tolerated.


References

  1. G. M. Robertson, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and G. Pattenden, Pergamon Press, Oxford, 1991, vol. 3, p. 563 Search PubMed; T. Wirth, Angew. Chem., 1996, 108, 65 Search PubMed; Angew. Chem., Int. Ed. Engl., 1996, 35, 61.
  2. (a) Y. Handa and J. Inanaga, Tetrahedron Lett., 1987, 28, 5717 CrossRef CAS; (b) A. W. Konradi, S. J. Kemp and S. F. Pedersen, J. Am. Chem. Soc., 1987, 109, 6551 CrossRef CAS; (c) M. C. Barden and J. Schwartz, J. Am. Chem. Soc., 1996, 118, 5484 CrossRef CAS.
  3. K. C. Nicolaou, Z. Yang, J. J. Chin, H. Ueno, P. G. Nantermet, R. K. Guy, C. F. Clairborne, J. Renaud, E. A. Coulardos, K. Paulvannan and E. J. Sorensen, Nature, 1994, 367, 630 CrossRef CAS.
  4. (a) H. Shinada, J.-P. Qü, H. Matsuzaka, Y. Ishii and Y. Hidai, Chem. Lett., 1995, 671 CAS; (b) R. Nomura, T. Matsuno and T. Endo, J. Am. Chem. Soc., 1996, 118, 11 666 CrossRef CAS.
  5. A. Fürstner and A. Hupperts, J. Am. Chem. Soc., 1995, 117, 4468 CrossRef; A. Fürstner and N. Shi, J. Am. Chem. Soc., 1996, 118, 2533 CrossRef.
  6. M. L. H. Green and C. R. Lucas, J. Chem. Soc., Dalton Trans., 1972, 1000 RSC; T. V. Rajan Babu and W. A. Nugent, J. Am. Chem. Soc., 1994, 116, 986 CrossRef CAS.
  7. J.-H. So, M.-K. Park and P. Boudjouk, J. Org. Chem., 1988, 53, 5871 CrossRef CAS.
  8. A. Clerici, L. Clerici and O. Porta, Tetrahedron Lett., 1996, 37, 3035 CrossRef CAS.
  9. R. L. Halterman, Chem. Rev., 1992, 92, 965 CrossRef CAS.
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