We have identified unactivated primary- and secondary homoallylic tosylates as substrates capable of oxidative addition to Pd-Quinox (quinoline-oxazoline) complexes at ambient temperature. The resultant Pd-alkyl species is prone to rapid �-hydride elimination, which affords an alkene and a Pd�H. These recombine via migratory insertion to afford a relatively stable allyl-Pd species that is readily coupled to a variety of aryl- and alkenyl boronate nucleophiles. Mechanistic data support an SN2-type stereoinvertive oxidative addition step, as well as a face-selective migratory insertion.

Palladium-catalyzed relay Suzuki cross-coupling reactions of unactivated primary- and secondary-alkyl electrophiles

246th National Meeting (2013)

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