Synthesis 2020; 52(18): 2639-2649
DOI: 10.1055/s-0040-1707860
short review
© Georg Thieme Verlag Stuttgart · New York

Oxidation of Alkynes via Catalytic Metal-Vinylidenes

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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: [email protected]   Email: [email protected]
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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: [email protected]   Email: [email protected]
› Author Affiliations
This work has received financial support from Ministerio de Economía y Competitividad (MINECO; project CTQ2017-87939R and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund – ERDF).
Further Information

Publication History

Received: 07 April 2020

Accepted after revision: 04 May 2020

Publication Date:
15 June 2020 (online)


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

 
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