Bronsted Acid Catalyzed 1,2-Silyl Shift in Propargyl Silanes: Synthesis of Silyl Dienes and Silyl Indenes
A general method for generation of allyl carbenium ions from propargyl silanes via a 1,2-silyl shift by Bronsted acids is reported. Two possible reaction pathways are described. Deprotonation results in silyl dienes with yields from 52% to 92%. Intramolecular Friedel-Crafts reactions of aryl-substituted systems give access to silyl indenes with yields of 18-90% depending on the substitution pattern. The obtained products have been shown to react as alkenyl silanes in Hiyama coupling and electrophilic substitution and as dienes in Diels-Alder cycloaddition. Copyright: CC BY-NC 4.0
Pieteikuma datums
27.07.2019.
Atslēgas vārdi
BiochemistryMicrobiologyGeneticsMolecular BiologyBiotechnologyEnvironmental SciencesChemical sciencesImmunologyDevelopmental BiologyInfectious diseasesPlant BiologyComputational Biologysilyl indenesSilyl Dienesaryl-substituted systemsBr onstedelectrophilic substitutionpropargyl silanesalkenyl silanesDeprotonation resultsreaction pathwaysallyl carbenium ionsYieldBr onsted acidssubstitution pattern
DOI
10.1021/acs.joc.8b02735.s001
