title: Efficient synthesis of an eta2-pyridine complex and a preliminary investigation of the bound heterocycle's reactivity.
abstract: Pyridine borane is combined with TpW(NO)(PMe(3))(eta(2)-benzene) to form a complex of the heterocycle, which upon treatment with acetone and acid yields the pyridinium complex [TpW(NO)(PMe(3))(eta(2)-pyH(+))]OTf. Deprotonation in the presence of acetic anhydride delivers the N-acetylpyridinium complex as a 10:1 mixture of coordination diastereomers. This acylpyridinium resists reaction with water or oxygen but readily reacts with acetone, pyrrole, indole, or acrolein and a weak base to stereoselectively form 1,2-dihydropyridine complexes. Treatment of the indole-derived analogue with CuBr(2) results in liberation of 3-(pyridin-2-yl)-1H-indole.
authors.affiliation: Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA.
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Harrison
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Welch
authors.forename: Adam C
authors.initials: AC
authors.lastname: Nielander
authors.forename: Michal
authors.initials: M
authors.lastname: Sabat
authors.forename: William H
authors.initials: WH
authors.lastname: Myers
authors.forename: W Dean
authors.initials: WD
authors.lastname: Harman