title: Palladium-catalyzed cross-coupling reactions between dihydropyranylindium reagents and aryl halides. synthesis of C-aryl glycals.
abstract: [reaction: see text] Palladium(0)-catalyzed cross-coupling reactions between tris(dihydropyranyl)indium 1 and aryl halides 2 have been investigated. Aryl iodides and electron-deficient aryl bromides couple efficiently with the in situ-generated indium reagents in the presence of 1-5 mol % Cl(2)Pd(PPh(3))(2) to produce substituted dihydropyrans 3 with minimal (<10%) dimer (4) formation. Organoindium reagents derived from D-glucal also undergo cross couplings with aryl iodides to produce C-aryl glycals.
authors.affiliation: Department of Chemistry, Harvey Mudd College, Claremont, California 91711, USA.
authors.forename: Ute
authors.initials: U
authors.lastname: Lehmann
authors.forename: Smita
authors.initials: S
authors.lastname: Awasthi
authors.forename: Thomas
authors.initials: T
authors.lastname: Minehan