title: Light-enabled synthesis of anhydrides and amides.
abstract: Recently, we have demonstrated that the photogeneration of Vilsmeier-Haack reagents is possible using only dimethylformamide (DMF) and tetrabromomethane (CBr4) in the bromination of alcohols. Extending these findings to carboxylic acid substrates has produced a mild and facile approach to the in situ formation of symmetric anhydrides, which were conveniently converted to amide derivatives in a one-pot process. The efficient protocols discussed herein are marked by use of UVA LEDs (365 nm), which have reduced the reaction times and come with a low setup cost.
authors.affiliation: Centre for Catalysis, Research and Innovation, Department of Chemistry, University of Ottawa , Ottawa, Ontario K1N 6N5, Canada.
authors.forename: Terry
authors.initials: T
authors.lastname: McCallum
authors.forename: Louis
authors.initials: L
authors.lastname: Barriault
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004126:Dimethylformamide / Q000737:chemistry*; D054879:Halogenation; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure; D055601:Organic Chemistry Phenomena
chemical_list: D000438:Alcohols; D000577:Amides; D000812:Anhydrides; D002264:Carboxylic Acids; D006842:Hydrocarbons, Brominated; D004126:Dimethylformamide; C005218:methyl bromide