Improved Procedure for Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl Halides with Aryltrimethoxysilanes under Solvent-Free Conditions

Abstract

An improved palladium-catalyzed Hiyama cross-coupling reaction is reported. In the presence of PdCl₂(MeCN)₂, P(o-tol)₃ and TBAF, a number of ArX (X = I, Br, Cl) were coupled with ArSi(OMe)₃ efficiently to afford the desired cross-coupled products in moderate to excellent yields. It is noteworthy that this protocol is conducted under relatively low Pd loadings and solvent-free conditions.

Key words

PdCl₂(MeCN)₂ - Hiyama cross-coupling reaction - aryl halide - arylsiloxane

References

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10

Only Pd(OAc)₂ as the Pd source was examined in reference 5a. We also attempted to reuse the PdCl₂(MeCN)₂/P(o-tol)₃/TBAF system, however, only a 48% yield of 3 was isolated in the second run.