title: Acetalization allows the photoheterolysis of the Ar-Cl bond in chlorobenzaldehydes and chloroacetophenones.
abstract: The nonaccessibility of phenyl cations by irradiation of electron-poor aryl chlorides was circumvented by transforming the carbonyl group of aromatic ketones or aldehydes into the corresponding 1,3-dioxolanes and the carboxyl group of benzoate ester into an orthoester functionality. This transformation allowed the heterolytic photoactivation of the Ar-Cl bond in protic media and the generation of phenyl cations. In the presence of π-bond nucleophiles, arylated products were obtained in good to excellent yields.
authors.affiliation: PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
authors.forename: Carlotta
authors.initials: C
authors.lastname: Raviola
authors.forename: Stefano
authors.initials: S
authors.lastname: Protti
authors.forename: Davide
authors.initials: D
authors.lastname: Ravelli
authors.forename: Mariella
authors.initials: M
authors.lastname: Mella
authors.forename: Angelo
authors.initials: A
authors.lastname: Albini
authors.forename: Maurizio
authors.initials: M
authors.lastname: Fagnoni
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D001128:Argon / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D015394:Molecular Structure; D055668:Photochemical Processes; D011789:Quantum Theory; D002721:omega-Chloroacetophenone / Q000737:chemistry*
chemical_list: D000080:Acetals; D001547:Benzaldehydes; D002712:Chlorides; D001128:Argon; D002721:omega-Chloroacetophenone; C059341:2-chlorobenzaldehyde; C052044:4-chlorobenzaldehyde