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Synthesis 2024; 56(15): 2295-2315
DOI: 10.1055/a-2197-7356
DOI: 10.1055/a-2197-7356
review
Organoselenium Compounds in Catalysis
This work was supported by grants from the Consejo Nacional de Investigaciones Científicas y Técnicas (PIP 112-202001-01544 CO), Agencia Nacional de Promoción Científica y Tecnológica (PICT-2018-03888), and the Universidad de Buenos Aires (20020170100067BA).
Abstract
In this article we have focused on the use of selenium in catalysis along with the proposed reaction mechanisms. With increasing interest in selenium chemistry, we have highlighted the most significant features of this subject, mainly in the last years. Selenium-containing catalysts have a key role in many transformations; for example, oxidation reactions that are performed under very mild and controlled conditions. In addition, utilizing the weak selenium–oxygen bonding interaction has proved to be very useful as a catalytic approach for specific transformations. The catalytic cycles of each appropriate transformation are fully reviewed.
1 Introduction
2 Use of Selenium in Catalysis: Perspectives
2.1 Selenium as Directing Group: Preparation of Organoselenium Compounds via C–H Borylation
2.2 Multicomponent Reactions Employing Selenium as a Catalyst
2.3 Selenium-π-Acid Catalysts
2.4 Electrochemical Selenium-Catalyzed Reactions
2.5 Stereoselective Synthesis Employing Organoselenium Catalysts
2.6 Transition-Metal Catalysts Containing Selenium-Based Ligands
2.6.1 Selenium-Ligated Palladium(II) Complexes as Catalysts for the Heck Reaction
2.6.2 Pincer Selenium Catalyst for the Allylation of Aldehydes and Closely Related Functional Groups
2.6.3 Selenium Employed in Buchwald-Type C–N Coupling Reactions
2.6.4 Organoselenium Catalysts in Suzuki–Miyaura Coupling Reactions
2.7 Organoselenium Catalysis in Michael-Type Reactions
2.8 Catalytic Cycle for Glutathione Peroxidase
2.9 Epoxidation
2.10 Dihydroxylation
2.11 Oxidation
2.12 Bromolactonization
2.13 Preparation of Alkenes from Vicinal Diols
2.14 Preparation of α-Selanyl Enals from Propargylic Alcohols
2.15 Miscellanea
3 Concluding Remarks
Key words
selenium - catalysis - organocatalysis - pincer catalysts - glutathione peroxidase - oxidationPublication History
Received: 19 July 2023
Accepted after revision: 24 October 2023
Accepted Manuscript online:
24 October 2023
Article published online:
02 January 2024
© 2024. Thieme. All rights reserved
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