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DOI: 10.1055/a-2114-7582
Halogenative Annulation Reactions of Alkyne-Tethered N- and O-Containing Arenes: Methods for Accessing Aryl-Fused Halogenated N- and O-Heterocycles
are grateful to Thailand Science Research and Innovation (36824/4274394, 36827/4274407, FRB660044/0240 Project Code 180850, FRB660044/0240 Project Code 180874), Mahidol University, Center of Excellence on Environmental Health and Toxicology (EHT), Office of Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI)
Dedicated to Prof. Guoqiang Lin’s contributions to organic chemistry
Abstract
Halogenative annulation of alkyne-tethered N- and O-containing arenes represents a general strategy for the construction of various halogenated N- and O-heterocycles. The methods employed are useful in producing valuable synthetic building blocks carrying C(sp2)–halide functional groups, which are useful synthetic handles, especially for cross-coupling reactions and a myriad of other transformations. When the alkyne is tethered to the heteroatom via an aromatic ring, the reaction gives rise to aryl-fused halogenated heterocycles. In this Short Review, various past and present halogenative annulation methods to construct aryl-fused halogenated N- and O-heterocycles are examined, with a focus on more recent technologies and the various roles of the participating halogenating agents. Additionally, future directions for this age-old, but still very useful, reaction are considered.
1 Introduction
2 Synthesis of Aryl-Fused Halogenated N-Heterocycles
2.1 Aryl-Fused Halogenated 5-Membered N-Heterocycles
2.2 Aryl-Fused Halogenated 6-Membered N-Heterocycles
2.3 Aryl-Fused Halogenated 7-Membered N-Heterocycles
3 Synthesis of Halogenated O-Heterocycles
3.1 Aryl-Fused Halogenated 5-Membered O-Heterocycles
3.2 Aryl-Fused Halogenated 6-Membered O-Heterocycles
3.3 Aryl-Fused Halogenated 7-Membered O-Heterocycles
4 Conclusion
Key words
alkynes - halogens - halogenative annulation - N-heterocycles - O-heterocycles - cyclization - halogenationPublication History
Received: 02 April 2023
Accepted after revision: 21 June 2023
Accepted Manuscript online:
21 June 2023
Article published online:
14 August 2023
© 2023. Thieme. All rights reserved
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