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Strain-Promoted Oxidative Annulation of Arynes and Cyclooctynes with Benzamides: Palladium-Catalyzed C–H/N–H Activation for the Synthesis of N-Heterocycles
Synthesis of Biaryls through Aromatic CH Bond Activation: A Review of Recent Developments
Abstract
This review describes recent progress made in the rapidly developing field of CH bond activation, in particular for syntheses of biaryls. The catalysts presented here provide convenient strategies for the direct arylation of arenes, via single or double CH bond activation, leading to inter-, and intramolecular carbon-carbon bond formation. The literature from mid-2009 to December 2013 has been discussed.
Free-Radical Cascade Alkylarylation of Alkenes with Simple Alkanes: Highly Efficient Access to Oxindoles via Selective (sp3)C–H and (sp2)C–H Bond Functionalization
lemuleFree-Radical Cascade Alkylarylation of Alkenes with Simple Alkanes: Highly Efficient Access to Oxindoles via Selective (sp3)C–H and (sp2)C–H Bond Functionalization
Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic Enynes
lemulesubstrate
Abstract
Aromatic enynes can be transformed into arylnaphthalenes or benzofulvenes depending on the reaction conditions. Under gold(I) catalysis, exclusive or major 6-endo-dig cyclization took place leading to arylnaphthalenes. However, a catalytic system based on palladium iodide/1,3-bis(diphenylphosphino)propane, in the presence of cesium carbonate as a base was necessary to furnish exclusively 5-exo-dig cyclization pattern, regardless of the electronic effects of the substituents. In the latter transformation, a mechanistic study (kinetic isotopic effect, density functional theory) involving a CH activation is suggested for the exclusive formation of benzofulvenes.