Cross-coupling reactions of arylsilanols with substituted aryl halides.
[reaction: see text] The palladium-catalyzed cross-coupling of arylsilanols with aryl iodides and aryl bromides (in the presence of cesium carbonate) furnished various biaryl products in high yield. An extensive series of optimizations led to the identification of key variables, including activator, solvent, catalyst, and hydration level, that influence the rate and selectivity of the process. Manipulation of these features provided an effective coupling method of wide scope and generality.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Ober
Michael H
MH
D001713:Biphenyl Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007202:Indicators and Reagents; D010165:Palladium / Q000737:chemistry; D012821:Silanes / Q000737:chemistry*
D001713:Biphenyl Compounds; D006842:Hydrocarbons, Brominated; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D012821:Silanes; D010165:Palladium