Efficient Synthesis of (E)-Vinylgermanes via Stille Cross-Coupling Reaction from 1-Tributylstannyl-2-trialkyl(triphenyl)germylethylenes

Abstract

The transfer of a β-vinylgermyl synthon is easily achieved by Stille reaction using (E)-1-tributylstannyl-2-trialkyl(or triphenyl)germylethylenes. With this methodology good yields of (E)-aryl or heteroarylvinylgermanes, stereodefined germyldienoic acids, and germyl α,β-enones are obtained from acid chlorides.

coupling reactions - organogermanium compounds - palladium catalyst

References

1

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2a Lesbre M. Mazerolles P. Satgé J. The Organic Compounds of Germanium   Wiley; New York: 1971. 

2b The Chemistry of Organic Germanium, Tin and Lead Compounds   Patai S. Rappoport Z. Wiley; Chichester: 1995. 

For some examples, see:

3a Ingold KU. Lusztyk J. Sciano JC. J. Am. Chem. Soc.  1984,  106:  343 

3b Nakamura T. Yokoyama Y. Mochida K. Synlett  1997,  907 

3c Ulrich I. Curran DP. J. Org. Chem.  1998,  63:  4711 

3d Nakano T. Enokido T. Noda S. Aihara N. Kosugi M. Migita T. J. Organomet. Chem.  1998,  553:  493 

3e Yorimitsu H. Shinokubo H. Oshima K. Synlett  1999,  1415 

4 Furukawa N. Kourogi N. Seki Y. Kakiuchi F. Murai S. Organometallics  1999,  18:  3764 

5 Matsubara S. Yoshino H. Utimoto K. Oshima K. Synlett  2000,  495 

6a Parrain J.-L. Duchêne A. Quintard J.-P. Tetrahedron Lett.  1990,  31:  1857 

6b Thibonnet J. Abarbri M. Parrain J.-L. Duchêne A. Tetrahedron Lett.  1996,  37:  7507 ; and references cited therein

7a Bottaro JC. Hanson RN. Seitz J. J. Org. Chem.  1981,  46:  5221 

7b Thibonnet J. Abarbri M. Parrain J.-L. Duchêne A. Synlett  1997,  771 

8a Stille JK. Angew. Chem., Int. Ed. Engl.  1986,  25:  508 

8b Mitchell TN. Synthesis  1992,  803 

8c Farina V. In Comprehensive Organometallic Chemistry II   Vol. 12:  Abel EW. Stone FG. Wilkinson G. Elsevier; Oxford: 1995.  Chap. 3.4. p.161-241  

8d Farina V. Roth GP. In Advances in Metal-Organic Chemistry   Vol.5:  Liebeskind LS. JAI Press; New York: 1996.  p.1-53  

8e Farina V. Krishnamurthy V. Scott WJ. Org. React.  1997,  50:  1 

8f Farina V. Krishnamurthy V. The Stille Reaction   Wiley; New York: 1999. 

9 For preliminary work, see: David-Quillot F. Thibonnet J. Marsacq D. Abarbri M. Duchêne A. Tetrahedron Lett.  2000,  41:  9981 

For some examples, see:

10a

Ref. [7b]

10b Abarbri M. Parrain J.-L. Kitamura M. Noyori R. Duchêne A. J. Org. Chem.  2000,  65:  7475 

10c Abarbri M. Parrain J.-L. Thibonnet J. Duchêne A. Synthesis  2002,  543