Organoselenium Compounds in Catalysis

Carola Gallo-Rodriguez; Juan B. Rodríguez

doi:10.1055/a-2197-7356

Synthesis, Table of Contents

Synthesis 2024; 56(15): 2295-2315
DOI: 10.1055/a-2197-7356

review

Organoselenium Compounds in Catalysis

Carola Gallo-Rodriguez

^aDepartamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, C1428EHA Buenos Aires, Argentina

^bCONICET-Universidad de Buenos Aires, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), C1428EHA Buenos Aires, Argentina

,

Juan B. Rodríguez ∗

^aDepartamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, C1428EHA Buenos Aires, Argentina

^cCONICET-Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos en Química Orgánica (UMYMFOR), C1428EHA Buenos Aires, Argentina

› Author Affiliations

Abstract

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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 - oxidation

Full Text

References

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