Adv. Synth. Catal., 2013, 355, 491–498

The practical process for the stereospecific cross-coupling of secondary allylic carbonates with arylboronic acids has been presented. The reaction catalyzed by in situ generated Pd nanoparticles (PdNPs) without any ligands and additional stabilizers in water under ambient conditions furnished allyl‒aryl coupling products in high level of isolated yields with high stereospecificities with excellent chemo-, regio- and E/Z selectivities. The in situ generated PdNPs showed extraordinary catalytic activity (s/c up to 5000) even for the allyl‒aryl coupling reaction of easily eliminated allylic carbonates under aqueous ambient conditions. The mechanism of the process has also been investigated.

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