title: Activation of C-H bonds via the merger of photoredox and organocatalysis: a coupling of benzylic ethers with Schiff bases.
abstract: The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C-H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical-radical coupling with secondary aldimines affords a variety of β-amino ether products in good to excellent yields. Mechanistic studies suggest that a reductive quenching pathway of the photocatalyst is operable.
authors.affiliation: Merck Center for Catalysis at Princeton University , Princeton, New Jersey 08544, United States.
authors.forename: Dominik
authors.initials: D
authors.lastname: Hager
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D012545:Schiff Bases / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D001593:Benzyl Compounds; D004987:Ethers; D007097:Imines; D009942:Organometallic Compounds; D012545:Schiff Bases; D013438:Sulfhydryl Compounds; D007495:Iridium