Abstract
Highly selective cross-coupling reaction of organosilanes with organic halides and organic triflates promoted by palladium catalyst and fluoride ion is described. Organosilicon compounds like (E) - or (Z) -alkenyl, alkynyl, allyl, and arylsilanes smoothly react with alkenyl, allyl and aryl halides to give coupled products with high chemoselectivity and stereospecificity. Under similar conditions, silylation of alkenyl iodides by hexa-methyldisilane and methylation of aryl iodides by (Et2N)3S+Me3SiF2- take place. The one-pot double cross-coupling of trimethylstannyl (trimethylsilyl) acetylene with two alkenyl iodides is achieved to afford isomerically pure dienynes. The cross-coupling of chiral 1-phenyl-1-trifluorosilylethane with aryl triflates occurrs stereo-specifically, providing optically active coupled products. The stereochemistry of the products is influenced decisively by reaction temperature and solvent used. A transition state model for the transmetallation step in catalytic cycle is proposed on the basis of substituent effect and stereochemical study of this reaction.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
