title: Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.
abstract: A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.
authors.affiliation: Department of Chemistry, University of Texas at San Antonio , One UTSA Circle, San Antonio, Texas 78249, United States.
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Larionov
authors.forename: David
authors.initials: D
authors.lastname: Stephens
authors.forename: Adelphe
authors.initials: A
authors.lastname: Mfuh
authors.forename: Gabriel
authors.initials: G
authors.lastname: Chavez
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D003497:Cyclic N-Oxides; D010165:Palladium; D003300:Copper