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Synthesis 2020; 52(04): 479-488
DOI: 10.1055/s-0039-1690720
DOI: 10.1055/s-0039-1690720
short review
Direct C(sp3)–H Activation of Carboxylic Acids
We thank the Max Planck Society (Otto Hahn Award to M.v.G.), the Fonds der Chemischen Industrie (Liebig Fellowship to M.v.G.), the Westfälische Wilhelms-Universität-Münster (WWU Münster) and the Deutsche Forschungsgemeinschaft (SFB858) for financial support.Further Information
Publication History
Received: 27 August 2019
Accepted after revision: 30 September 2019
Publication Date:
17 October 2019 (online)
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
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For selected reviews on C–H activation, see:
Monomeric palladium carboxylates exist in complex equilibria with dimeric and trimeric species in solution, which depends on various parameters. The problems associated with the desired C–H activation processes of carboxylic acids are discussed on the monomeric complexes for simplicity. For representative publications dealing with this matter, see:
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