title: Complex N-heterocycle synthesis via iron-catalyzed, direct C-H bond amination.
abstract: The manipulation of traditionally unreactive functional groups is of paramount importance in modern chemical synthesis. We have developed an iron-dipyrrinato catalyst that leverages the reactivity of iron-borne metal-ligand multiple bonds to promote the direct amination of aliphatic C-H bonds. Exposure of organic azides to the iron dipyrrinato catalyst furnishes saturated, cyclic amine products (N-heterocycles) bearing complex core-substitution patterns. This study highlights the development of C-H bond functionalization chemistry for the formation of saturated, cyclic amine products and should find broad application in the context of both pharmaceuticals and natural product synthesis.
authors: Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA.
authors: Elisabeth T
authors: ET
authors: Hennessy
authors: Theodore A
authors: TA
authors: Betley
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001384:Azetidines / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D055598:Chemical Phenomena; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000588:Amines; D001384:Azetidines; D001386:Azides; D006571:Heterocyclic Compounds; D008024:Ligands; D010880:Piperidines; D011759:Pyrrolidines; C082735:azetidine; C032727:piperidine; D007501:Iron