title: Smooth photocatalytic preparation of 2-substituted 1,3-benzodioxoles.
abstract: A mild and general method for the synthesis of potentially bioactive 2-substituted-1,3-benzodioxoles is presented. This is based on the photocatalyzed activation of methylene hydrogen atoms in the presence of tetrabutylammonium decatungstate (TBADT). The method gave yields ranging from 46-77 % with no interference by benzene ring substituents, such as OR, COOMe, Me, or CHO. The OH group interfered, but protection regenerated the reactivity. 5-Chloro-1,3-benzodioxole was converted into a safrole derivative through a one-pot process involving two consecutive irradiations, at 366 nm for the photocatalyzed alkylation at position 2 and at 310 nm for the alkylation at position 5.
authors.affiliation: Department of Organic Chemistry, University of Pavia, Via Taramelli 10, Italy.
authors.forename: Davide
authors.initials: D
authors.lastname: Ravelli
authors.forename: Angelo
authors.initials: A
authors.lastname: Albini
authors.forename: Maurizio
authors.initials: M
authors.lastname: Fagnoni
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004149:Dioxoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D055668:Photochemical Processes
chemical_list: D000475:Alkenes; D004149:Dioxoles; C040539:1,3-benzodioxole