Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes.

Abstract : 2H-Azirines are easily synthesized from the corresponding ketones and, despite possessing a CN bond embedded in a strained three-membered cycle, they are sufficiently stable to be isolated, stored, and manipulated. 2H-Azirines can be regarded as valuable synthetic equivalents of alkenyl nitrenes, however, reactions capitalizing on the cyclic strain of the heterocyclic motif and involving the cleavage of the CN single bond remain surprisingly limited. A gold-catalyzed reaction that allows the formation of polysubstituted functionalized pyridines from easily accessible 2-propargyl 2H-azirine derivatives was developed. This transformation, which corresponds to an unprecedented intramolecular transfer of an alkenyl nitrene to an alkyne, proceeds with low catalyst loading, is efficient, and exhibits a high functional-group tolerance and a wide substrate scope.
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Submitted on : Thursday, June 5, 2014 - 11:40:08 AM
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Agnes Prechter, Guilhem Henrion, Pierre Faudot Dit Bel, Fabien Gagosz. Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes.. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2014, 53 (19), pp.4959-63. ⟨10.1002/anie.201402470⟩. ⟨hal-01001934⟩

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