A Novel, Simple and Efficient Synthesis of Ferrocenyl Enones and Alkynols

Abstract

A mild and efficient alkoxide-catalyzed addition of ferrocenylacetylene to diverse ketones and aldehydes is described. Some new propargyl alcohols containing ferrocenyl moieties were obtained by addition of ferrocenylacetylene to ketones. When aromatic aldehydes were used, trans-enones such as ferrocenyl chalcone derivatives were obtained in high yields via base-catalyzed addition-isomerization.

Key words

ferrocenylacetylene - propargylic alcohols - aromatic aldehydes - enones - alkynylation.

References

• 1 Glasby JS. Encyclopedia of the Alkaloids   Plenum Press; New York: 1975. 
• 2a Borzilleri RM. Weinreb SM. Parvez M. J. Am. Chem. Soc.  1995,  117:  10905 
• 2b Zhu G. Lu XI. J. Org. Chem.  1995,  60:  1087 
• 2c Mukai C. Kataoka O. Hanaoka M. J. Org. Chem.  1993,  58:  2946 
• 3a Cadiot P. Chodkiewicz W. Chemistry of Alkylenes   Marcel Dekker; New York: 1969. 
• 3b Hurdlik PE. Hurdlik AM. In The Chemistry of the Carbon-Carbon Triple Bond   Patai S. John Wiley and sons; New York: 1978. 
• 3c Smith WN. Kuehn ED. J. Org. Chem.  1973,  38:  3588 
• 4 Brown HC. Molander GA. Singh SM. Racherla US. J. Org. Chem.  1985,  50:  1577 
• 5 Ahn JH. Joung MJ. Yoon NM. Oniciu DC. Katritzky AR. J. Org. Chem.  1999,  64:  488 
• 6 Imamoto T. Sugiura Y. Takiyama N. Tetrahedron Lett.  1984,  25:  4233 
• 7 Hirao T. Misu D. Agawa T. Tetrahedron. Lett.  1986,  27:  933 
• 8 Babler JH. Liptak VP. Phan N. J. Org. Chem.  1996,  61:  416 
• 9 Tzalis D. Knochel P. Angew. Chem. Int. Ed.  1999,  38:  1463 
• 10 Lin JT. Wu JJ. Li CS. Wen YS. Lin KJ. Organometallics  1996,  15:  5028 
• 11 Ferrocenes   Togni A. Hayashi T. Wiley-VCH; Weinheim: 1995. 
• 12 Long NJ. Angew. Chem., Int. Ed. Engl.  1995,  34:  21 
• 13 Nguyen P. Gómez-Elipe P. Manners I. Chem. Rev.  1999,  99:  1515 
• 14a Boichard J. Morin JP. Tiroutlef J. Bull. Soc. Chim. Fr.  1963,  851 
• 14b Nesmeyanov AN. Zagorevskii DV. Nekrasov YS. Sizoi VF. Postnov VM. Baran AM. Klimova EI. J. Organomet. Chem.  1979,  169:  77 
• 15a Müller TJJ. Ansorge M. Aktah D. Angew. Chem. Int. Ed.  2000,  39:  1253 
• 15b Andres J. Cardenas R. Silla E. Tapia O. J. Am. Chem. Soc.  1988,  110:  666