Aryne-Based Multicomponent Coupling Reactions

Sourav Ghorai; Daesung Lee

doi:10.1055/s-0039-1690824

Synlett, Table of Contents

Synlett 2020; 31(08): 750-771
DOI: 10.1055/s-0039-1690824

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Aryne-Based Multicomponent Coupling Reactions

Sourav Ghorai

,

Daesung Lee ∗

Abstract

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Abstract

Multicomponent reactions (MCRs) constitute a powerful synthetic tool to generate a large number of small molecules with high atom economy, which thus can efficiently expand the chemical space with molecular diversity and complexity. Aryne-based MCRs offer versatile possibilities to construct functionalized arenes and benzo-fused heterocycles. Because of their electrophilic nature, arynes couple with a broad range of nucleophiles. Thus, a variety of aryne-based MCRs have been developed, the representative of which are summarized in this account.

1 Introduction

2 Aryne-Based Multicomponent Reactions

2.1 Trapping with Isocyanides

2.2 Trapping with Imines

2.3 Trapping with Amines

2.4 Insertion into π-Bonds

2.5 Trapping with Ethers and Thioethers

2.6 Trapping with Carbanions

2.7 Transition-Metal-Catalyzed Approaches

3 Strategies Based on Hexadehydro Diels–Alder Reaction

3.1 Dihalogenation

3.2 Halohydroxylation and Haloacylation

3.3 Amides and Imides

3.4 Quinazolines

3.5 Benzocyclobutene-1,2-diimines and 3H-Indole-3-imines

3.6 Other MCRs of Arynes and Isocyanides

4 Conclusion

Key words

arynes - multicomponent reactions - Diels–Alder reaction - silver - heterocycles

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References

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