Lewis acid-mediated Suzuki–Miyaura Cross-Coupling Reaction

13 August 2021, Version 3
This content is a preprint and has not undergone peer review at the time of posting.


The palladium-catalysed Suzuki–Miyaura cross-coupling (SMC) reaction of organohalides and organoborons is a reliable method for carbon–carbon bond formation. This reaction involves a base-mediated transmetalation process, but the presence of a base also promotes competitive protodeborylation, which reduces the efficiency. Herein, we established an SMC reaction via Lewis acid-mediated transmetalation of an organopalladium(II) intermediate with organoborons. Experimental and theoretical investigations indicate that the controlled release of the transmetalation-active intermediate enabled base-independent transmetalation under heating conditions and enhanced the applicable scope of this process. This system enabled us to avoid the addition of a base, and thus, rendered substrates with base-sensitive moieties available. Results from this research further expand the overall utility of cross-coupling chemistry.


Suzuki–Miyaura cross‐coupling reaction
base-free methodology
Lewis acid additive

Supplementary materials

Supplementary Information, including additional figures, tables, Cartesian coordinates of optimized structures, and NMR spectra.


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