π-Acid Mediated Insertion of Alkynes into Carbon–Heteroatom σ-Bonds

Abstract

The rapidly expanding field of gold and platinum π-acid catalysis has led to the discovery of diverse transformations that are initiated with nucleophilic attack onto a metal-activated alkyne. This review brings together those reactions which employ a heteroatom nucleophile bearing a functional group that can subsequently migrate to effect a formal insertion of the alkyne into a carbon–heteroatom­ σ-bond. This reactivity profile is encountered in a range of efficient and powerful cycloisomerisations for the preparation of carbo- and heterocycles.

1 Introduction

2 1,2-Addition of Carbon–Heteroatom Bonds across Alkynes

2.1 Heteroatom-to-Carbon Allyl Migrations

2.2 Accessing Sigmatropic Rearrangements

2.3 Related Palladium-Catalysed 1,2-Carboalkoxylations and Carboaminations

2.4 Beyond Allyl Migration in the 1,2-Carbofunctionalisation of Alkynes

2.5 Oxonium Ion Migration

2.6 Migrating Centres at Higher Oxidation Levels

2.7 Migration of Heteroatoms

3 1,5 Heteroatom-to-Carbon Migrations

3.1 Alkynyl Benzoates as Alkylating Agents

4 Internal versus External Migrations

4.1 Internal Migrations of Oxonium Species

5 1,1-Carbofunctionalisations

6 Application in Natural Products

7 Summary and Conclusions

Key words

catalysis - gold - platinum - alkynes - nucleophilic addition - cyclisation - heterocycles

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