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Campagne, J.-M.  et al.: 2024 Science of Synthesis, 2024/1: Knowledge Updates 2024/1 DOI: 10.1055/sos-SD-120-00150
Knowledge Updates 2024/1

20.5.1.7.16 Catalytic α-Arylation of Alkyl Alkanoates

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Editors: Campagne, J.-M. ; Donohoe, T. J.; Fürstner, A. ; Jiang, X. ; Wang, M. 

Authors: Cheng, J. ; Chowdhury, S. ; Harris, P. A. ; Li, X. ; Liu, M. ; Liao, L.; Song, Q. ; Tang, R.-Y. ; Tobrman, T. ; Wang, L.; Wu, X.-F. ; Ying, J. ; Yu, J.-S. ; Zhang, Y.

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

Also available at
 


Abstract

α-Aryl carboxylic esters are important motifs or precursors in a wide variety of drugs, bioactive natural products, and pharmacologically active compounds. This chapter is an update to enrich the original Science of Synthesis chapter dedicated to the synthesis of alkyl alkanoates “Synthesis with Retention of the Functional Group” (Section 20.5.1.7). The current review focuses on recent advances in the catalytic α-arylation of alkyl alkanoates, and describes methods for the synthesis of α-aryl carboxylic compounds reported in the period 2001–2022. Seven main approaches are introduced: α-arylations of alkyl esters or their enolates, α-arylations of Reformatsky reagents with aryl halides, α-arylations of silyl ketene acetals, α-arylations of α-halo esters, α-arylations of α-diazo esters, decarboxylative or deacetylative α-arylation of β-carbonyl esters, and reductive C—O bond arylation of oxalates derived from α-hydroxy esters.

Key words

arylation - alkyl alkanoates - arylating agents - transition-metal catalysis - organocatalysis
 
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