Late-Stage β-C(sp3)–H Deuteration of Carboxylic Acids

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

Abstract

Carboxylic acid moieties are highly abundant in bioactive molecules. In this study we describe the late-stage β C(sp3)–H deuteration of free carboxylic acids. Based on our finding that the C–H activation with our catalyst systems is reversible, the de-deuteration process was first optimized. The resulting conditions involve a novel type of ligands, which, amongst other positions, for the first time enables the functionalization of non-activated methylene β-C(sp3)–H bonds and can be used to achieve the desired deuteration when using a deuterated solvent. The reported method allows for the functionalization of a wide range of free carboxylic acids with diverse substitution patterns, as well as the late-stage deuteration of bioactive molecules and related frameworks.

Keywords

C–H activation
hydrogen isotope exchange
late-stage functionalization
carboxylic acids
deuteration

Supplementary materials

Title
Description
Actions
Title
Uttry et al Deuteration
Description
Actions
Title
Uttry et al Deuteration 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.