Repurposing cycloaddition of β-carbonyl phosphonate and azide to synthesize triazolyl phosphonates via ionic-liquid-based data-driven screening†
*a
and
Lingjun
Li
*ab
Abstract
Phosphonic acids represent a class of important structural units widely found in natural products and artificially synthesized functional molecules. Nature uses β-carbonyl phosphonic acid as a versatile building block to access structurally diverse phosphonic acid derivatives, which inspires a biomimetic way for chemists, however, it is limited by the detrimental tendency of C–P bond cleavages during chemical reactions. To address this challenge, we here developed an ionic-liquid-based data-driven screening (ILDDS), an approach that can comprehensively employ multifunctional effects of ionic liquids for discovering new reactivity, developing potent synthetic reactions, and even simplifying bioactivity evaluations. Using ILDDS, we repurposed the cycloaddition of β-carbonyl phosphonate and azide to synthesize triazolyl phosphonates that usually produced phosphonate-leaving products under the traditional conditions. And then, the repurposed cycloaddition reaction allows the access of triazolyl phosphonates bearing various substituents under mild conditions. Furthermore, an integrative workflow combining modular and combinational syntheses, simple purification, and in situ bioactivity evaluation can be de novo designed and implemented in a high throughput way, finally leading to fast acquirements of phosphonate compounds for inhibiting the growth of Rhizoctonia solani.
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