Dehydrohalogenation of isomeric 2- and 3-bromomethyl substituted 2,3-dihydrooxazolo[3,2-a]pyridines

Iodine(I) and Silver(I) Complexes Incorporating 3-Substituted Pyridines

“…There is precedence for the stabilization of carbocations with a pair of Lewis bases in a directly analogous fashion to bis (pyridine)­iodine­(I) complexes, which may play a role in the mechanism . Additionally, the synthesis of analogous N-alkylated-β-halogenated compounds upon reaction of aromatic amines and alkenes has been reported. − A tentative mechanism could therefore be suggested from the initial formation of 2-methyl-2-pentene from propene (itself from i Pr + ) that in turn reacts with a liberated 3-acetaminopyridine ligand and a source of I + (either the iodine­(I) complex 1b or the in situ generated IO i Pr) to give 1d . This is supported by the knowledge that 2-methyl-2-pentene can be directly formed from i PrOH, with i PrOI also being a potential chemical precursor.…”

Pd-Catalyzed Regio- and Enantioselective Aminoarylation of Allenols with Aryl Iodides and 2-Pyridones

“…Interestingly, the bicyclic pyridium salt 9 bearing three stereocenters can be obtained in 75% yield with complete diastereoselectivity. The hydrolysis 20 of compound 9 with aqueous K 2 CO 3 proceeded smoothly to afford more functionalized chiral 2-pyridone compound 10 as an only diastereomer in 85% yield without any deterioration of enantiomeric purity (Scheme 3c). The absolute configurations of 7 and 9 were unambiguously assigned by X-ray crystallography (see the Supporting Information).…”