Organic Chemistry Portal

Abstracts

Search:

Palladium-Catalyzed Cross-Coupling Reactions of Substituted Aryl(dimethyl)silanols

Scott E. Denmark*, Michael H. Ober

*Roger Adams Laboratory, Department of Chemistry University of Illinois, Urbana, Illinois 61801, Email: denmarkscs.uiuc.edu

S. E. Denmark, M. H. Ober, Adv. Synth. Catal., 2004, 346, 1703-1715.

DOI: 10.1002/adsc.200404204 (free Supporting Information)


Abstract

Cesium carbonate and cesium hydroxide monohydrate are effective activators for the palladium-catalyzed cross coupling of electron-rich aryl(dimethyl)silanols with aryl iodides and aryl bromides. Extensive optimization led to the identification of key variables such as solvent, catalyst, and hydration level.

see article for more examples



Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides

S. E. Denmark, R. C. Smith, W.-T. T. Chang, J. M. Muhuhi, J. Am. Chem. Soc., 2008, 131, 3104-3118.


Key Words

Hiyama-Denmark Coupling, biaryls, C-C bond formation, cesium carbonate, cesium hydroxide, fluoride-free, hydration effect


ID: JXX-Y2004-2460