Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.
This Account chronicles the conceptual development, proof of principle, exploration of scope, and mechanistic investigations of a newly developed class of palladium-catalyzed cross-coupling reactions of silicon derivatives. Under the influence of fluoride activation a myriad of oxygen-containing silicon moieties undergo mild and stereospecific cross-coupling. The diversity of methods for introduction of silicon groupings into organic molecules and the range of organic electrophiles that can be used are outlined.
Denmark
Scott E
SE
245 Roger Adams Laboratory, Box 18, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Sweis
Ramzi F
RF
D002384:Catalysis; D004987:Ethers / Q000737:chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*
D004987:Ethers; D017646:Organosilicon Compounds; D010165:Palladium; D010100:Oxygen; D012825:Silicon