ArticleBioconjugate chemistry2021
Arylethynyltrifluoroborate Dienophiles for on Demand Activation of IEDDA Reactions.
Article in Bioconjugate chemistry, 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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Who cites it
3 citing papers in PubMed.
- An Untethered and Formal Intermolecular Hexadehydro-Diels-Alder Reaction: Alkynylboronates with 2-(1,3-Butadiynyl)pyridines.Journal of the American Chemical Society · 2024Article
- Minimalist TetrazineJournal of the American Chemical Society · 2024Article
- Alkynone β-trifluoroborates: A new class of amine-specific biocompatible click reagents.Science advances · 2023Article
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Authors and funding
9 authors.
Funding
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Abstract
Strained alkenes and alkynes are the predominant dienophiles used in inverse electron demand Diels-Alder (IEDDA) reactions. However, their instability, cross-reactivity, and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for fast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g., pyridyl- to benzyl-substituents), cycloaddition kinetics can vary from fast (
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