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

Ilya M. Lyapkalo*, Michael A. K. Vogel, Ekaterina V. Boltukhina, Jiří Vavřík

*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, E. V. Boltukhina, J. Vavřík, Synlett, 2009, 558-561.

DOI: 10.1055/s-0028-1087919 (free Supporting Information)


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Abstract

Terminal and internal acetylenes were obtained in good to excellent isolated yields from carbonyl compounds by converting the carbonyl functionality into the enol nonaflate intermediate followed by elimination to give the C-C triple bond. The one-pot transformations were uniformly induced by phosphazene bases combined with mildly electrophilic nonafluorobutane-1-sulfonyl fluoride.

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

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


Key Words

alkynes (terminal alkynes, internal alkynes), eliminations, regioselectivity, nonafluoro­butane-1-sulfonyl fluoride, phosphazene bases


ID: J60-Y2009-0640