Cross-coupling of alkynylsilanols with aryl halides promoted by potassium trimethylsilanolate.
The palladium-catalyzed cross-coupling of aliphatic alkynylsilanols with aryl iodides has been demonstrated with potassium trimethylsilanolate as the coupling promoter and copper(I) iodide as a cocatalyst. The cross-coupling proceeds at room temperature in good to excellent yield with a range of aryl iodides. A comparison of the reactivity of alkynylsilanols, trimethylsilylalkynes, and terminal alkynes under fluoride and fluoride-free conditions was performed to elucidate the role of silicon in the Sonogashira reaction.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL 61801, USA. denmark@scs.uiuc.edu
Tymonko
Steven A
SA
D006219:Halogens / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D006219:Halogens; D014297:Trimethylsilyl Compounds; C482968:potassium trimethylsilanolate