title: Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.
abstract: Friedel-Crafts amidoalkylation was achieved by oxidation of dialkylamides using persulfate (S(2)O(8)(2-)) in the presence of the visible light catalyst, Ru(bpy)(3)Cl(2), at room temperature, via a reactive N-acyliminium intermediate. Alternatively, mild heating of the dialkylamides and persulfate afforded a metal and Lewis acid-free Friedel-Crafts amidoalkylation. Alcohols and electron-rich arenes served as effective nucleophiles, forming new C-O or C-C bonds. In general, photocatalysis provided higher yields and better selectivities.
authors.affiliation: Department of Chemistry, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Chunhui
authors.initials: C
authors.lastname: Dai
authors.forename: Francesco
authors.initials: F
authors.lastname: Meschini
authors.forename: Jagan M R
authors.initials: JM
authors.lastname: Narayanam
authors.forename: Corey R J
authors.initials: CR
authors.lastname: Stephenson
mesh_terms: D000478:Alkylation; D002384:Catalysis; D008027:Light; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010777:Photochemistry; D010782:Photolysis; D012428:Ruthenium / Q000737:chemistry*; D013696:Temperature; D013818:Thermogravimetry
chemical_list: D009942:Organometallic Compounds; D012428:Ruthenium