Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes
Authors:
- 6 September 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (38) , 14916-14919
Abstract
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.Keywords
This publication has 34 references indexed in Scilit:
- Palladium-Catalyzed Cycloisomerizations of (Z)-1-Iodo-1,6-dienes: Iodine Atom Transfer and Mechanistic Insight to Alkyl Iodide Reductive EliminationJournal of the American Chemical Society, 2011
- Carboxylate-Assisted Transition-Metal-Catalyzed C−H Bond Functionalizations: Mechanism and ScopeChemical Reviews, 2011
- Palladium-Catalyzed Carboiodination of Alkenes: Carbon−Carbon Bond Formation with Retention of Reactive FunctionalityJournal of the American Chemical Society, 2011
- The Role of Reversible Oxidative Addition in Selective Palladium(0)-Catalyzed Intramolecular Cross-Couplings of Polyhalogenated Substrates: Synthesis of Brominated IndolesJournal of the American Chemical Society, 2010
- A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights intogem-Dibromoolefin ReactivityOrganic Letters, 2010
- Palladium-Catalyzed Ligand-Directed C−H Functionalization ReactionsChemical Reviews, 2010
- Palladium(II)‐Catalyzed C-H Activation/C-C Cross‐Coupling Reactions: Versatility and PracticalityAngewandte Chemie International Edition, 2009
- Reductive Elimination of Aryl Halides upon Addition of Hindered Alkylphosphines to Dimeric Arylpalladium(II) Halide ComplexesOrganometallics, 2004
- Directly Observed Reductive Elimination of Aryl Halides from Monomeric Arylpalladium(II) Halide ComplexesJournal of the American Chemical Society, 2003
- Reductive Elimination of Aryl Halides from Palladium(II)Journal of the American Chemical Society, 2001