Insights Into Palladium-Catalyzed Cyanation of Bromobenzene: Additive Effects on the Rate-Limiting Step
- 3 November 2008
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (23), 5325-5328
- https://doi.org/10.1021/ol8016935
Abstract
Kinetic studies using reaction calorimetry were conducted under synthetically relevant conditions to study the effect of additives in the cyanation of bromobenzene catalyzed by palladium complexes. This work demonstrates that the addition of a catalytic amount of ZnBr2 facilitates the reaction with an elimination of the induction period observed without additive. This study afforded a qualitative assessment of the effect of water on the rate-limiting step and the apparent reaction order in bromobenzene.Keywords
This publication has 30 references indexed in Scilit:
- Development of a Mild and Robust Method for Large-Scale Palladium-Catalysed Cyanation of Aryl Bromides: Importance of the Order of AdditionOrganic Process Research & Development, 2008
- Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed Suzuki, Heck, Sonogashira, and cyanation reactionsTetrahedron, 2008
- Mechanisms of Catalyst Poisoning in Palladium-Catalyzed Cyanation of Haloarenes. Remarkably Facile C−N Bond Activation in the [(Ph3P)4Pd]/[Bu4N]+ CN- SystemJournal of the American Chemical Society, 2008
- Open air palladium catalyzed cyanation—the use of PMHS to protect from oxygenTetrahedron Letters, 2007
- Mild and General Methods for the Palladium-Catalyzed Cyanation of Aryl and Heteroaryl ChloridesOrganic Letters, 2007
- Why Excess Cyanide Can Be Detrimental to Pd-Catalyzed Cyanation of Haloarenes. Facile Formation and Characterization of [Pd(CN)3(H)]2- and [Pd(CN)3(Ph)]2-Journal of the American Chemical Society, 2006
- Ligand-Free Palladium-Catalyzed Cyanation of Aryl HalidesThe Journal of Organic Chemistry, 2005
- Progress in the Palladium‐Catalyzed Cyanation of Aryl ChloridesChemistry – A European Journal, 2003
- Palladium-catalyzed cyanation reactions of aryl chloridesTetrahedron Letters, 2000
- Nucleophilic Displacement Catalyzed by Transition Metal. I. General Consideration of the Cyanation of Aryl Halides Catalyzed by Palladium(II)Bulletin of the Chemical Society of Japan, 1975