Origin of Protonation Side Products in Pd-Catalyzed Decarboxylative Allylation Reactions: Evidence for In Situ Modification of Triphenylphosphine Ligand

02 February 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Palladium-catalyzed decarboxylative allylation (DcA) is a well-established method of carbon-carbon bond formation. This type of coupling is quite attractive, as the only byproduct is CO2. While a wide variety of ligands have been employed with Pd(0) or Pd(II) precatalysts in DcA reactions, the ligand structure is most often based on a triarylphosphine core. Despite their demonstrated utility, DcA processes have been hindered by the formation of protonation side products. While this phenomenon has been widely acknowledged, little has been reported on the origin of the proton. Herein, we address this and provide multiple lines of experimental evidence for the proton originating from the triarylphosphine ligand.


decarboxylative allylation
protonation side product

Supplementary materials

Origin of Protonation Side Products in Decarboxylative Allylation Reactions v1 SupportingInfo


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.