ArticleChemical science2021
Silicon as a powerful control element in HDDA chemistry: redirection of innate cyclization preferences, functionalizable tethers, and formal bimolecular HDDA reactions.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- 1The Journal of organic chemistry · 2026Article
- Utilizing the Pentadehydro-Diels-Alder Reaction for Polycyclic Aromatic Compound Synthesis: Diels-Alder-Based Linker Transformation.Molecules (Basel, Switzerland) · 2025Article
- An Untethered and Formal Intermolecular Hexadehydro-Diels-Alder Reaction: Alkynylboronates with 2-(1,3-Butadiynyl)pyridines.Journal of the American Chemical Society · 2024Article
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3 authors.
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Abstract
The 1,3-diyne and diynophile in hexadehydro-Diels-Alder (HDDA) reaction substrates are typically tethered by linker units that consist of C, O, N, and/or S atoms. We describe here a new class of polyynes based on silicon-containing tethers that can be disposed of and/or functionalized subsequent to the HDDA reaction. The cyclizations are efficient, and the resulting benzoxasiloles are amenable to protodesilylation, halogenation, oxygenation, and arylation reactions. The presence of the silicon atom can also override the innate mode of cyclization in some cases, an outcome attributable to a β-silyl effect on the structure of intermediate diradicals. Overall, this strategy equates formally to an otherwise unknown, bimolecular HDDA reaction and expands the versatility of this body of aryne chemistry.
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