Inexpensive and Efficient Synthesis of Propargylic Substituted Active Methylene Compounds Catalyzed by FeCl₃

Abstract

A highly efficient and practical method for the synthesis of propargylic substituted 1,3-dicarbonyl compounds with direct use of propargylic alcohols in the presence of inexpensive and environmentally benign FeCl₃ (5 mol%) has been presented. The reaction works with varieties of substrates at room temperature without an inert atmosphere with an excellent yield. The present method can also be employed for the large-scale synthesis of propargylic substituted active methylene compounds.

Keywords:

• Atom economical
• carbon–carbon bond
• iron salt
• propargylic alcohols
• sustainable chemistry

ACKNOWLEDGMENTS

We gratefully acknowledge the financial and infrastructural support from the University Grants Commission–Center of Advanced Study (UGC-CAS) program of the Department of Chemistry, Jadavpur University. S. M. and S. B. are also thankful to the UGC, Jadavpur University and New Delhi, India, respectively, for their fellowships.

Notes

^a The yields refer to pure isolated products obtained after column chromatography and characterized by spectral data.

^b 1.2 eq. alcohol was used.

^c The reaction was carried out in 1:1 dichloromethane/1,4 dioxan solvent at 50 °C.

^a The yields refer to pure isolated product obtained after column chromatography and characterized by spectral data.

^b 1.2 eq. alcohol was used.

^c The reaction worked in nitromethane solvent.

^d The reaction worked at 60 °C in nitromethane solvent.

^e Room temperature for 3 h, then reflux for 5 h.