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.

Abstract

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.

Keywords

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

Supplementary materials

Title
Description
Actions
Title
TNsi1813
Description
Supplementary Information, including additional figures, tables, Cartesian coordinates of optimized structures, and NMR spectra.
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.