Gold Vinylidenes as Useful Intermediates in Synthetic Organic Chemistry

Fabien Gagosz

doi:10.1055/s-0037-1611647

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(05): 1087-1099
DOI: 10.1055/s-0037-1611647

short review

Copyright with the author

Gold Vinylidenes as Useful Intermediates in Synthetic Organic Chemistry

Fabien Gagosz *

Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5, Ottawa, Canada Email: fgagosz@uottawa.ca

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Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Gold vinylidenes have recently emerged as useful intermediates in synthetic organic chemistry. These species, which can principally be accessed by a 1,2-migration process from a gold-activated alkyne or by dual gold catalysis on a diyne substrate, can react with nucleophilic partners or by C–H insertion to produce a variety of functionalized (poly)cyclic compounds. This short review covers the synthetic approaches developed so far to access gold vinylidenes and the different reactivities these species can exhibit.

1 Introduction

2 1,2-Migration Processes

3 Dual Gold Catalysis

4 Other Processes

5 Conclusion

Key words

vinylidene - reactive intermediate - gold - catalysis - dual catalysis - nucleophilic trapping - C–H insertion

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References

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