Gold‐Catalyzed Synthesis of Functionalized Pyridines by Using 2H‐Azirines as Synthetic Equivalents of Alkenyl Nitrenes1. Issue 19 (8th April 2014)

• Record Type: Journal Article
• Authors: Prechter, Agnes; Henrion, Guilhem; Faudot dit Bel, Pierre; Gagosz, Fabien
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 19(2014)
• Page Start: 4959
• Page End: 4963
• Publication Date: 2014-04-08
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201402470
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>2<italic>H</italic>‐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. 2<italic>H</italic>‐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.</p> </abstract>