Palladium-catalyzed oxidative intermolecular difunctionalization of terminal alkenes with organostannanes and molecular oxygen.
A cationic palladium complex catalyzes the title transformations, which are thought to proceed via a pi-allyl or pi-benzyl intermediate. The regioselectivity of the reaction (1,2- or 1,1-difunctionalization) depends on the type of terminal double bond (conjugated or nonconjugated) in the substrate (see scheme) and appears to be controlled by the relative rates of beta-hydride elimination and transmetalation. DMA=dimethylacetamide, Tf=triflyl.
Urkalan
Kaveri Balan
KB
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112, USA.
Sigman
Matthew S
MS
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D009947:Organotin Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
D000475:Alkenes; D009947:Organotin Compounds; D010165:Palladium; D010100:Oxygen