New Efficient Preparation of Functionalized Arylzinc or Thienylzinc ­Compounds from Aryl or Thienyl Chlorides Using Cobalt Catalysis

Abstract

A new chemical method is described for the preparation of aryl or thienyl zinc intermediates from their corresponding aromatic or thienyl chlorides in a mixture of acetonitrile-pyridine, using cobalt catalysis. This procedure allows for the synthesis of a variety of functionalized arylzinc species from reactive arylchlorides or chlorothiophenes in good to excellent yields. Some of these arylzinc compounds have been coupled with aromatic bromides using palladium catalysis.

Key words

cobalt halide - catalysis - zinc - thiophenes - aromatic chlorides

References

• 1 Ikegami R. Koresawa A. Shibata T. Takagi K. J. Org. Chem.  2003,  68:  2195 
• 2 Kneisel FF. Dochnahl M. Knochel P. Angew. Chem. Int. Ed.  2004,  43:  1017 
• 3 Tucker CE. Majid TN. Knochel P. J. Am. Chem. Soc.  1992,  114:  3983 
• 4 Krasovskiy A. Knochel P. Angew. Chem. Int. Ed.  2004,  43:  3333 
• 5a Zhu L. Wehmeyer RM. Rieke RD. J. Org. Chem.  1991,  56:  1445 
• 5b Rieke RD. Aldrichimica Acta  2000,  33:  52 
• 6a Sibille S. Ratovelomanana V. Périchon J. J. Chem. Soc., Chem. Commun.  1992,  283 
• 6b Gosmini C. Nédélec J.-Y. Périchon J. Tetrahedron Lett.  1997,  38:  1941 
• 7a Gosmini C. Rollin Y. Nédélec J.-Y. Périchon J. J. Org. Chem.  2000,  65:  6024 
• 7b Fillon H. Gosmini C. Nédélec J.-Y. Périchon J. Tetrahedron Lett.  2001,  42:  3843 
• 7c Fillon H. Le Gall E. Gosmini C. Périchon J. Tetrahedron Lett.  2002,  43:  5941 
• 8a Fillon H. Gosmini C. Périchon J. J. Am. Chem. Soc.  2003,  125:  3867 
• 8b Kazmierski I. Gosmini C. Paris J.-M. Périchon J. Tetrahedron Lett.  2003,  44:  6417 
• 9 Buriez O. Nédélec J.-Y. Périchon J. J. Electroanal. Chem.  2001,  506:  162