Stereoselective Synthesis of <i>Cis</i>- and <i>Trans</i>-Tetrasubstituted Vinyl Silanes Using a Silyl-Heck Strategy and Hiyama Conditions for Their Cross-Coupling
Michael F. Wisthoff, Sarah B. Pawley, Andrew P. Cinderella, Donald A. Watson
Abstract
We report a palladium-catalyzed, three-component carbosilylation reaction of internal symmetrical alkynes, silicon electrophiles, and primary alkyl zinc iodides. Depending on the choice of ligand, stereoselective synthesis of either cis- or trans-tetrasubstituted vinyl silanes is possible. We also demonstrate conditions for the Hiyama cross-coupling of these products to prepare geometrically defined tetrasubstituted alkenes.
Topics & Concepts
ChemistrySilanesStereoselectivityElectrophileAlkylSilylationHeck reactionZincLigand (biochemistry)Organic chemistryPolymer chemistryCatalysisArylSilaneBiochemistryReceptorCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistryCatalytic C–H Functionalization Methods