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A General and Versatile Method for CC Cross-Coupling Synthesis of Conjugated Enynes: One-Pot Sequence Starting from Carbonyl Compounds

Ilya M. Lyapkalo, Michael A. K. Vogel

*Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo n. 2, 166 10 Prague 6, Czech Republic, Email: ilya.lyapkalouochb.cas.cz

I. M. Lyapkalo, M. A. K. Vogel, Angew. Chem. Int. Ed., 2006, 45, 4019-4023.

DOI: 10.1002/anie.200504594 (free Supporting Information)


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Abstract

A straightforward one-pot approach to highly diverse conjugated enynes, starting from carbonyl precursors has been developed. The low nucleophilic phosphazene bases, which are used for the generation of the alkenyl nonaflates and the terminal alkynes, are compatible with NfF and do not impede the subsequent Sonogashira reaction.

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A General One-Step Synthesis of Alkynes from Enolisable Carbonyl Compounds

I. M. Lyapkalo, M. A. K. Vogel, E. V. Boltukhina, J. Vavřík, Synlett, 2009, 558-561.


Key Words

Sonogashira coupling, cross-coupling, enynes, homogeneous catalysis, phosphazene bases


ID: J06-Y2006-1560