Deacylative Alkylation vs. Photoredox Catalysis in the Synthesis of 3,3'‐Bioxindoles

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Title: Deacylative Alkylation vs. Photoredox Catalysis in the Synthesis of 3,3'‐Bioxindoles
Authors: Moreno-Cabrerizo, Cristina | Ortega-Martínez, Aitor | Esteruelas, Miguel A. | López, Ana M. | Nájera, Carmen | Sansano, Jose M.
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Deacylative alkylation | Dacylative bromination | Bioxindoles | Iridium | Photoredox catalysis
Knowledge Area: Química Orgánica
Issue Date: 29-May-2020
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2020, 20: 3101-3109. doi:10.1002/ejoc.202000375
Abstract: The synthesis of 3,3'‐bioxindoles employing deacylative alkylations (DaA) in one‐pot process, where the 3‐bromooxindoles are generated in situ, is described. Good yields and moderate diastereoselections are obtained. By the modification of this procedure the synthesis of pure 3‐bromooxindoles through a deacylative bromination (DaB) is achieved. These bromides are efficiently employed in a photoredox dimerization process to get the desired 3,3'‐bioxindoles in good yields and low diastereoselections. In this single‐electron‐transfer (SET) mechanism the presence of a high quantum‐yield iridium(III) complex ensures high conversions in short reaction times.
Sponsor: We gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (projects CTQ2016-81893REDT, and RED2018-102387-T) the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P, CTQ2016-80375-P and CTQ2017-82935-P), the Generalitat Valenciana (PROMETEOII/2014/017), the University of Alicante, and Gobierno de Aragón (Group E06_17R and project LMP148_18). A. O.-M. thanks MINECO for a predoctoral fellowship.
URI: http://hdl.handle.net/10045/107015
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.202000375
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: https://doi.org/10.1002/ejoc.202000375
Appears in Collections:INV - SINTAS - Artículos de Revistas

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