title: Late-stage functionalization of biologically active heterocycles through photoredox catalysis.
abstract: The direct CH functionalization of heterocycles has become an increasingly valuable tool in modern drug discovery. However, the introduction of small alkyl groups, such as methyl, by this method has not been realized in the context of complex molecule synthesis since existing methods rely on the use of strong oxidants and elevated temperatures to generate the requisite radical species. Herein, we report the use of stable organic peroxides activated by visible-light photoredox catalysis to achieve the direct methyl-, ethyl-, and cyclopropylation of a variety of biologically active heterocycles. The simple protocol, mild reaction conditions, and unique tolerability of this method make it an important tool for drug discovery.
authors.affiliation: Department of Process Chemistry, Merck Research Laboratories, 90 E. Scott Ave., Rahway, NJ 07065 (USA). daniel.dirocco@merck.com.
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Dirocco
authors.forename: Kevin
authors.initials: K
authors.lastname: Dykstra
authors.forename: Shane
authors.initials: S
authors.lastname: Krska
authors.forename: Petr
authors.initials: P
authors.lastname: Vachal
authors.forename: Donald V
authors.initials: DV
authors.lastname: Conway
authors.forename: Matthew
authors.initials: M
authors.lastname: Tudge
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010777:Photochemistry
chemical_list: D006571:Heterocyclic Compounds
keywords: homogeneous catalysis; photoredox catalysis; radical reactions; visible light