What does this research mean for the field?

A newly developed 1,3-benzdiyne precursor enables the chemoselective, sequential generation and regioselective trapping of two aryne triple bonds on a single aromatic ring, providing modular access to 1,2,3,4-substitution motifs. Novelty: ClaimNovelty.METHODOLOGICAL. Consensus alignment: ConsensusAlignment.NEUTRAL.

What question did this study set out to answer?

To develop a versatile precursor enabling the chemoselective and sequential generation of two aryne triple bonds from a single aromatic ring under mild conditions.

September 8, 2026The Journal of Organic ChemistryOpen Access

Chemoselective Generation of the 1,3-Benzdiyne Synthon

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To develop a versatile precursor enabling the chemoselective and sequential generation of two aryne triple bonds from a single aromatic ring under mild conditions.
Synthesized a single benzene scaffold functionalized with an iodonium leaving group and an ortho-silylaryl triflate moiety.
Initiated the first aryne via base-mediated deprotonation and the second aryne via fluoride activation, carrying out regioselective trapping reactions at each stage.
Performed density functional theory (DFT) calculations to evaluate the ground state distortion and electronic structure of both aryne intermediates.
Achieved controlled, sequential generation and regioselective trapping of two aryne triple bonds on the same ring under mild conditions.
DFT modeling demonstrated high-to-very high levels of ground state distortion in both aryne systems governing regioselectivity.
Established a modular synthetic pathway providing access to densely functionalized 1,2,3,4-substituted arene frameworks.

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Implication

Synthetic chemistry study reveals chemoselective sequential aryne generation on a single benzene ring, facilitating modular access to complex 1,2,3,4-substituted arenes.

Cite This Study

Barnå et al. (2026) studied this question.

synapsesocial.com/papers/6a9fd79b58e84d0ff5b466c9 https://doi.org/10.1021/acs.joc.6c00616

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Implication

Synthetic chemistry study reveals chemoselective sequential aryne generation on a single benzene ring, facilitating modular access to complex 1,2,3,4-substituted arenes.

Chemoselective Generation of the 1,3-Benzdiyne Synthon

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Discussion

Implication

Cite This Study

Chemoselective Generation of the 1,3-Benzdiyne Synthon

Key Points

Discussion

Implication

Cite This Study

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