Direct C(sp³)–H Activation of Carboxylic Acids

Published as part of the Bürgenstock Special Section 2019Future Stars in Organic Chemistry

Abstract

Carboxylic acids are important in a variety of research fields and applications. As a result, substantial efforts have been directed towards the C–H functionalization of such compounds. While the use of the carboxylic acid moiety as a native directing group for C(sp²)–H functionalization reactions is well established, as yet there is no general solution for the C(sp³)–H activation of aliphatic carboxylic acids and most endeavors have instead relied on the introduction of stronger directing groups. Recently however, novel ligands, tools, and strategies have emerged, which enable the use of free aliphatic carboxylic acids in C–H-activation-based transformations.

1 Introduction

2 Challenges in the C(sp³)–H Bond Activation of Carboxylic Acids

3 The Lactonization of Aliphatic Carboxylic Acids

4 The Directing Group Approach

5 The Direct C–H Arylation of Aliphatic Carboxylic Acids

6 The Direct C–H Olefination of Aliphatic Carboxylic Acids

7 The Direct C–H Acetoxylation of Aliphatic Carboxylic Acids

8 Summary

Key words

carboxylic acids - C–H activation - native directing group - synthetic methodology

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