Mild and Chemoselective Carboxylic Acid Reduction Promoted by Borane Catalysis.

Autor: Lunic D; Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany., Sanosa N; Department of Chemistry, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios 53, 26006, Logroño, Spain., Funes-Ardoiz I; Department of Chemistry, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios 53, 26006, Logroño, Spain., Teskey CJ; Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2022 Oct 24; Vol. 61 (43), pp. e202207647. Date of Electronic Publication: 2022 Sep 21.
DOI: 10.1002/anie.202207647
Abstrakt: Although considerable advances have been made in developing chemoselective transformations of ubiquitous carboxylic acid groups, many challenges still exist. For instance, their selective reduction is problematic if both more nucleophilic and more electrophilic groups are present in the starting material. Here, we address this problem with a simple and mild protocol using bench-stable reagents at ambient temperatures. This platform is able to tolerate a diverse range of functionality, leaving ketones, esters, nitro-groups, olefins, nitriles and amides untouched. A combination of experimental and computational mechanistic experiments demonstrate that this reaction proceeds via hidden borane catalysis with small quantities of in situ generated BH 3 playing a key role in the exquisite selectivity that is observed.
(© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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