Synlett 2020; 31(12): 1147-1157
DOI: 10.1055/s-0039-1690861
account
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Ruthenium-Catalyzed Carbene/Alkyne Metathesis (CAM) Transformations

Damián Padín
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: carlos.saa@usc.es
,
,
Carlos Saá
› Institutsangaben
This work has received financial support from the Ministerio de Economía y Competitividad (MINECO, projects 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). D.P. thanks the Ministerio de Educación, Cultura y Deporte for a predoctoral FPU fellowship (Grant Number FPU15/02132).
Weitere Informationen

Publikationsverlauf

Received: 17. Februar 2020

Accepted after revision: 02. März 2020

Publikationsdatum:
31. März 2020 (online)


Abstract

Carbene intermediates have shown versatile applications in modern synthetic chemistry. Catalytic ruthenium carbene/alkyne metathesis (CAM) with readily available substrates renders an efficient procedure for the in situ generation of ruthenium vinyl carbene intermediates. Here, recent advances in synthetic applications of ruthenium-catalyzed carbene/alkyne metathesis (CAM) are highlighted.

1 Introduction

2 Ruthenium Vinyl Carbenes through Carbene/Alkyne Metathesis (CAM)

3 Nonpolar Transformations of Ruthenium Vinyl Carbenes

4 Polar Transformations of Ruthenium Vinyl Carbenes

4.1 Intramolecular Ruthenium-Catalyzed [1,5]- and [1,6]-Hydride Transfer/Cyclization

4.2 Heterocyclizations of Alkynals and Alkynones

4.3 Heterocyclizations of ortho-(Alkynyloxy)benzylamines

5 DFT Studies on the Stereoselectivity of the CAM Reaction

6 Conclusions