Bench-Stable and Recoverable Palladium(I) Dimer as an Efficient Catalyst for Heck Cross-Coupling

Abstract

The application of air- and moisture-stable dinuclear palladium(I) complex [Pd(μ-I)(Pt-Bu₃)]₂ as an efficient catalyst for the Heck cross-coupling reaction of aryl iodides and bromides with acrylates and styrenes is described. The developed protocol is robust and operationally simple and shows a high functional-group tolerance. The employed palladium(I) dimer catalyst is highly robust under these nucleophilic as well as elevated-temperature conditions, allowing its recovery after reaction completion and recycling.

Key words

palladium(I) dimer - cross-coupling - Heck reaction - dinuclear catalysis - alkenes - catalyst recycling

• References

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Mayr’s scale is based on the addition of nucleophiles to carbocations and Michael acceptors; see:
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• 14 ³¹P NMR only shows the presence of the free phosphine ligand t-Bu₃P. This is most likely a result of fast conversion of the Pd(I)–bromo dimer to the monophosphine Pd(0)–Pt-Bu₃, an accumulation of which leads to decomposition to Pd black and free phosphine ligand. Please see ref. 12 for further information.