Synthesis of functionalized CF3-containing heterocycles via [2,3]-sigmatropic rearrangement and sequential catalytic carbocyclization |
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Authors: | Daria V VorobyevaArtur K Mailyan Alexander S PeregudovNatalia M Karimova Tamara P VasilyevaIvan S Bushmarinov Christian BruneauPierre H Dixneuf Sergey N Osipov |
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Institution: | a A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russian Federation b Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France |
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Abstract: | A new efficient access to functionalized CF3-substituted and nitrogen or sulfur-containing heterocycles has been developed directly from diazocompounds CF3C(N2)Z (Z=CO2Me, P(O)(OEt)2). The method is based on the direct selective synthesis of doubly unsaturated substrates followed by metal-mediated carbocylization. The first step has been performed by Cu(II)-catalyzed 2,3]-sigmatropic rearrangement of propargyl- or/and allyl-containing sulfur and nitrogen ylides leading to fluorinated enynes, diolefins, and especially allenynes derivatives. The second step involves their carbocyclization via ring closing metathesis and Pauson-Khand reaction. |
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Keywords: | Fluorinated diazocompounds Sigmatropic rearrangement Allenynes Enynes Catalysis Carbocyclization Heterocycles |
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