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Synlett 2020; 31(08): 750-771
DOI: 10.1055/s-0039-1690824
DOI: 10.1055/s-0039-1690824
account
Aryne-Based Multicomponent Coupling Reactions
We thank the National Science Foundation (CHE-1764141) for financial support.Weitere Informationen
Publikationsverlauf
Received: 17. Januar 2020
Accepted after revision: 25. Januar 2020
Publikationsdatum:
20. März 2020 (online)
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
-
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