20.5. 13.2 Arenecarboxylic Acid Esters (Update 2024)
Book
Editors: Campagne, J.-M. ; Donohoe, T. J.; Fürstner, A. ; Jiang, X. ; Wang, M.
Title: Knowledge Updates 2024/1
Online ISBN: 9783132457058; Book DOI: 10.1055/b000000967
1st edition © 2024 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Laboratory Techniques, Stoichiometry;Organometallic Chemistry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
![](https://www.thieme-connect.de/media/10.1055-b000000967/thumbnails/a_102tbw.jpg)
Arenecarboxylic acid esters are prevalent motifs in pharmaceuticals, agrochemicals, polymers, and natural products. They are also versatile building blocks in organic synthesis. Traditionally, esters are prepared via activation of acids or acid anhydrides, followed by nucleophilic substitution. However, these methods usually require harsh reaction conditions and two steps. Over the past couple of decades, alternative synthetic approaches have been developed, including Chan—Lam-type reactions, oxidative esterification, carbonylation, and addition of carboxylic acids to unsaturated carbon—carbon bonds. This review highlights recent developments of these transformations with some selected works reported between 2002 and 2022, and serves as an update to the previous (2007) Science of Synthesis chapter on the preparation of arenecarboxylic acid esters (Section 20.5.13).
Key words
arenecarboxylic acid esters - Chan—Lam-type reactions - oxidative esterification - carbonylation - addition of carboxylic acids - ester synthesis-
4 Hulsman N, Medema JP, Bos C, Jongejan A, Leurs R, Smit MJ, de Esch IJP, Richel D, Wijtmans M. J. Med. Chem. 2007; 50: 2424
-
6 Nagamitsu T, Marumoto K, Nagayasu A, Fukuda T, Arima S, Uchida R, Ohshiro T, Harigaya Y, Tomoda H, Ōmura S. J. Antibiot. 2009; 62: 69
- 9 Comprehensive Organic Transformations: A Guide to Functional Group Preparations. Larock RC. Wiley VCH; New York 1999
-
12 Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC. Chem. Rev. 2013; 113: 6234 Chem. Rev. 2014; 114: 899.
-
30 Maruani A, Lee MTW, Watkins G, Akhbar AR, Baggs H, Shamsabadi A, Richards DA, Chudasama V. RSC Adv. 2016; 6: 3372
-
35 Dong J, Chen X, Ji F, Liu L, Su L, Mo M, Tang J.-S, Zhou Y. Appl. Organomet. Chem. 2021; 35: e6073
-
36 Subaramanian M, Ramar PM, Rana J, Gupta VK, Balaraman E. Chem. Commun. (Cambridge) 2020; 56: 8143