Palladium-Catalyzed Decarboxylative 1,2-Addition of Carboxylic Acids to Glyoxylic Acid Esters

  • The formation of C−C-bonds constitutes one of the most fundamental synthetic operations in organic chemistry. The nucleophilic addition of preformed organometallic reagents to an electrophilic carbonyl functionality represents a classical method for the selective construction of a C−C-bond. However, the synthesis and utilization of an organometallic reagent is associated with an unfavorable environmental profile. Herein, we disclose a Palladium-catalyzed decarboxylative 1,2-addition of carboxylic acids to glyoxylic acid esters. This novel method provides access to the mandelic acid scaffold in good yields. Easy-to-handle and readily available benzoic acids are utilized as more sustainable alternative to preformed organometallic nucleophiles.

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Metadaten
Author:Bastian Jakob, Ichraf Slimani, Andreas Diehl, Naceur Hamdi, Georg Manolikakes
URN:urn:nbn:de:hbz:386-kluedo-80398
DOI:https://doi.org/10.1002/ejoc.202100919
ISSN:1099-0690
Parent Title (English):European Journal of Organic Chemistry
Publisher:Wiley
Document Type:Article
Language of publication:English
Date of Publication (online):2024/04/16
Year of first Publication:2021
Publishing Institution:Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau
Date of the Publication (Server):2024/04/16
Issue:2021/46
Page Number:7
First Page:6340
Last Page:6346
Source:https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100919
Faculties / Organisational entities:Kaiserslautern - Fachbereich Chemie
DDC-Cassification:5 Naturwissenschaften und Mathematik / 540 Chemie
Collections:Open-Access-Publikationsfonds
Licence (German):Zweitveröffentlichung