title: Regioselective, Transition Metal-Free C-O Coupling Reactions Involving Aryne Intermediates.
abstract: A new transition-metal-free synthetic method for C-O coupling between various aryl halides and alkoxides is described. This type of transformation is typically accomplished using palladium catalysts containing a specialized phosphine ligand. The reactions reported here can be performed under mild, ambient conditions using certain potassium alkoxides and a range of aryl halides, with iodide and bromide derivatives giving the best results. A likely mechanistic pathway involves the in situ generation of an aryne intermediate, and directing groups on the aryl ring inductively control regioselectivity.
authors.affiliation: Department of Chemistry, University of California , Berkeley, Berkeley, California 94720, United States.|Chemical Sciences Division, Lawrence Berkeley National Laboratory , Berkeley, California 94720, United States.
authors.forename: Yuyang
authors.initials: Y
authors.lastname: Dong
authors.affiliation: Department of Chemistry, University of California , Berkeley, Berkeley, California 94720, United States.|Chemical Sciences Division, Lawrence Berkeley National Laboratory , Berkeley, California 94720, United States.
authors.forename: Michael I
authors.initials: MI
authors.lastname: Lipschutz
authors.affiliation: Department of Chemistry, University of California , Berkeley, Berkeley, California 94720, United States.|Chemical Sciences Division, Lawrence Berkeley National Laboratory , Berkeley, California 94720, United States.
authors.forename: T Don
authors.initials: TD
authors.lastname: Tilley