Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.

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Ruthenium-catalyzed nucleophilic ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols were investigated. When a neutral ruthenium(II) catalyst, Cp*RuCl(COD), was used in MeOH, the trans-1,2-ring opened product was formed as the only regio- and stereoisomer. On the other hand, when a cationic ruthenium(II) catalyst, [CpRu(CH(3)CN)(3)]PF(6), was used in MeOH, the cis-1,2-ring opened product was formed exclusively. Moderate to excellent stereoselectivity (70:30 to 100:0) was observed with various alcohols.