Oxidation of Alkynes via Catalytic Metal-Vinylidenes

Andrea Álvarez-Pérez; Carlos Saá; Jesús A. Varela

doi:10.1055/s-0040-1707860

Synthesis, Table of Contents

Synthesis 2020; 52(18): 2639-2649
DOI: 10.1055/s-0040-1707860

short review

Oxidation of Alkynes via Catalytic Metal-Vinylidenes

Andrea Álvarez-Pérez

,

Carlos Saá ∗

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain Email: jesus.varela@usc.es Email: carlos.saa@usc.es

,

Jesús A. Varela ∗

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain Email: jesus.varela@usc.es Email: carlos.saa@usc.es

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Abstract

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Abstract

Metal-vinylidenes, generated by treatment of terminal alkynes with transition metals, are very useful intermediates in modern synthetic chemistry as shown by the high number of transformations in which they are involved. When a metal-vinylidene is generated in the presence of an oxidant, its immediate oxidation to a ketene occurs. In this short review, recent synthetic applications of the oxidation of alkynes via ketene intermediates from initially formed metal-vinylidenes are highlighted.

1 Introduction

2 Oxidation of Metal-Vinylidenes with Internal Oxidants

3 Oxidation of Metal-Vinylidenes with External Oxidants

4 Conclusions

Key words

amides - cyclization - esters - β-lactams - ketenes - vinylidenes

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References

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