title: Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates.
abstract: Single-electron transmetalation is recognized as an enabling technology for the mild transfer of alkyl groups to transition metal catalysts in cross-coupling reactions. Hypercoordinate silicates represent a new and improved class of radical precursors because of their low oxidation potentials and the innocuous byproducts generated upon oxidation. Herein, we report the cross-coupling of secondary and primary ammonium alkylsilicates with (hetero)aryl bromides in good to excellent yields. The base-free conditions have exceptional protic group tolerance on both partners, permitting the cross-coupling of unprotected primary and secondary amines.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Jouffroy
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: David N
authors.initials: DN
authors.lastname: Primer
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
mesh_terms: D064751:Ammonium Compounds / Q000737:chemistry*; D002384:Catalysis; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D017640:Silicates / Q000737:chemistry*
chemical_list: D064751:Ammonium Compounds; D017640:Silicates; D009532:Nickel