title: Oxidative Cross-Coupling of sp(3)- and sp(2)-Hybridized C-H Bonds: Vanadium-Catalyzed Aminomethylation of Imidazo[1,2-a]pyridines.
abstract: The vanadium-catalyzed oxidative coupling of substituted 2-arylimidiazo[1,2-a]pyridines to N-methylmorpholine oxide, which acts as both a coupling partner and an oxidant, has been achieved. This reaction was applied to various substituted imidiazo[1,2-a]pyridine and indole substrates, resulting in yields as high as 90%. Mechanistic investigations indicate that the reaction may proceed via a Mannich-type process. This work demonstrates how oxidative aminomethylation can be used as a useful method to introduce tertiary amines into heterocycles, thus providing an alternative method for conventional Mannich-type reactions.
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science , Pilani, Rajasthan 333031, India.
authors.forename: Pinku
authors.initials: P
authors.lastname: Kaswan
authors.affiliation: Department of Chemistry, University of Rhode Island , 51 Lower College Road, Kingston, Rhode Island 02881, United States.
authors.forename: Ashley
authors.initials: A
authors.lastname: Porter
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science , Pilani, Rajasthan 333031, India.
authors.forename: Kasiviswanadharaju
authors.initials: K
authors.lastname: Pericherla
authors.affiliation: Department of Chemistry, University of Rhode Island , 51 Lower College Road, Kingston, Rhode Island 02881, United States.
authors.forename: Marissa
authors.initials: M
authors.lastname: Simone
authors.affiliation: Department of Chemistry, University of Rhode Island , 51 Lower College Road, Kingston, Rhode Island 02881, United States.
authors.forename: Sean
authors.initials: S
authors.lastname: Peters
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science , Pilani, Rajasthan 333031, India.
authors.forename: Anil
authors.initials: A
authors.lastname: Kumar
authors.affiliation: Department of Chemistry, University of Rhode Island , 51 Lower College Road, Kingston, Rhode Island 02881, United States.
authors.forename: Brenton
authors.initials: B
authors.lastname: DeBoef
mesh_terms: D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D058451:Oxidative Coupling; D011725:Pyridines / Q000737:chemistry*; D014639:Vanadium / Q000737:chemistry*
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; D007093:Imidazoles; D009025:Morpholines; D016877:Oxidants; D011725:Pyridines; D014639:Vanadium; C038816:4-methylmorpholine