Palladium‐Catalyzed Alkenylation of Azaarylmethylamines with Vinyl Halides

Abstract

Abstract A general and versatile alkenylation protocol for the synthesis of vinyl‐azaarylmethylamines has been developed. Enabled by a palladium/NIXANTPHOS catalyst, this protocol provides efficient access to a large variety of N ‐heterocycles bearing allylic amines in up to 98% yield. A wide variety of azaarylmethylamines bearing 2‐pyridylmethyl, 4‐pyridylmethyl, 2‐(aminomethyl)quinoline aryl motifs and diverse 5 to 7 membered cyclic amines were well tolerated. A gram scale reaction was also used to demonstrate the scalability. This method can be readily adopted by medicinal chemists to prepare valuable scaffolds that were previously difficult to access. magnified image