Benzyne acts as a chemical reaction intermediate.
Extensive chemical literature consistently characterizes benzyne (and arynes generally) as high-energy, reactive chemical intermediates that are generated from various precursors and rapidly trapped or polymerized.
The retrieved papers overwhelmingly confirm that benzyne acts as a transient, highly reactive chemical intermediate in various organic synthesis and mechanistic pathways.
Xu Q, Hoye TR. Free carbenes from complementarily paired alkynes.. 2024. https://doi.org/10.1038/s41557-024-01550-9
Paper 0 describes arynes as high-energy, reactive intermediates.
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Preston-Herrera C, Devin RC, Matter ME, Stache EE. Aryne Generation from Aryl Halides Via Photothermal Red-Light Activation.. 2025. https://doi.org/10.1021/jacs.5c14686
Paper 1 discusses the generation and trapping of high-energy aryne intermediates.
Kaicharla T, Jin M, Hoye TR. An Untethered and Formal Intermolecular Hexadehydro-Diels-Alder Reaction: Alkynylboronates with 2-(1,3-Butadiynyl)pyridines.. 2024. https://doi.org/10.1021/jacs.4c11622
Paper 2 demonstrates the formation of benzyne intermediates captured by trapping agents.
Sneddon DS, Kevorkian PV, Hoye TR. Rapid (≤25 °C) cycloisomerization of anhydride-tethered triynes to benzynes - origin of a remarkable anhydride linker-induced rate enhancement.. 2025. https://doi.org/10.1039/d4sc07232d
Paper 3 details hexadehydro-Diels-Alder reactions generating ortho-benzyne derivatives.
Walters ZG, Witkowski DC, Houk KN, Garg NK. Mechanisms of Kobayashi eliminations for the generation of highly strained arynes, cyclic cumulenes, and anti-Bredt olefins.. 2025. https://doi.org/10.1039/d5sc03943f
Paper 4 examines transient strained intermediates, specifically benzyne, via Kobayashi eliminations.
Lee S, Hoye TR. Cycloadditions of Benzynes with the Azoxy [RN═N<sup>+</sup>(O<sup>-</sup>)R'] 1,3-Dipole Tautomer of 1-Hydroxybenzotriazole (HOBT).. 2024. https://doi.org/10.1021/acs.orglett.4c01819
Paper 5 explores cycloadditions of thermally generated benzynes as reactive species.
Sonobe M, Kitazawa Y, Uchiyama M, Kimura M. Copper-mediated stepwise polymerization of benzynes: construction of amphiphilic block copolymers and their self-assembly in water.. 2026. https://doi.org/10.1039/d6ra01918h
Paper 7 describes the direct polymerization of benzynes generated from precursors.
Tyerman S, Clark KF, Stewart AJ, Kolodziejczak K, Robertson CM, Evans L, Kennedy AR, Tuttle T, Nelson DJ, Murphy JA. How Alkali Metal Alkoxides Initiate Organic Radical Reactions.. 2026. https://doi.org/10.1021/jacs.5c22122
Paper 8 shows that deprotonation leads to benzynes that initiate radical chemistry.
Kraemer N, Hoye TR. 1<i>H</i>-Isoindolynes: Arynes Accessible by a One-Pot, Ambient Temperature, Three-Component Cascade.. 2026. https://doi.org/10.1021/acs.joc.5c03027
Paper 9 introduces isoindolynes as a new type of aryne generated via cascade reactions.
Ikeshita D, Atarashi M, Yoshikai N. Ring-Opening Arylation of Cyclic Diaryliodoniums via Cyclic Triaryliodanes as Aryne Precursors and Dynamic Aryl Reservoirs.. 2026. https://doi.org/10.1002/anie.6935149
Paper 10 notes the use of cyclic diaryliodoniums as precursors to arynes.
Hart JD, Lawrence JK, Franqui PN, Perrott DR, Yi B, Xi Y, Sumby CJ, Newton CG, George JH. Biomimetic Synthesis of Seven Halenaquinone Meroterpenoids.. 2026. https://doi.org/10.1021/jacs.6c06760
Paper 11 utilizes an aryne-furan Diels-Alder reaction to construct complex carbon frameworks.
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