Ligand-Enabled γ-C(sp3)–H Olefination of Free Carboxylic Acids

18 February 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report the ligand enabled C(sp3)–H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.

Keywords

γ-C(sp3)–H activation
Carboxylic AcidsA
δ-Lactones
Ligand-Enabled Catalysis
Palladium

Supplementary materials

Title
Description
Actions
Title
Ghosh Uttry et al olefination SI
Description
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.