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<p>Functionalized oxetanes and azetidines are promising bioisosteres, yet their inclusion in agrochemical and pharmaceutical candidate screening remains limited due to a lack of viable synthetic methods. Herein, we utilize XtalFluor-E<sup>®</sup> to prepare 3,3-arylamino oxetanes and 3,3-arylamino azetidines in moderate-to-high yields (30–97%) using a mild, one-step deoxyamination strategy. This work establishes a direct deoxyamination using suflur (IV) fluoride reagents. We coupled experimental screening with multivariate linear regression (MLR) analysis to gain greater insight regarding factors that influence the reaction scope. Furthermore, experiments paired with density functional theory (DFT) calculations provided key mechanistic insight into the nucleophilic substitution reactions at the sulfur(IV) center. The simplicity and short reaction times of our protocol facilitates the library syntheses of these key bioisosteres.</p><p></p>

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One pot sulfur(IV) fluoride-mediated deoxyaminations for the syntheses of 3,3-arylamino oxetanes and azetidines

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年5月29日

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  • Brodie J. Thomson,
  • Jiajing Li,
  • Sean L. Betteridge,
  • Dillon Thiesen,
  • Maximilian Bagus,
  • Jolene P. Reid,
  • Glenn M. Sammis

摘要

Functionalized oxetanes and azetidines are promising bioisosteres, yet their inclusion in agrochemical and pharmaceutical candidate screening remains limited due to a lack of viable synthetic methods. Herein, we utilize XtalFluor-E® to prepare 3,3-arylamino oxetanes and 3,3-arylamino azetidines in moderate-to-high yields (30–97%) using a mild, one-step deoxyamination strategy. This work establishes a direct deoxyamination using suflur (IV) fluoride reagents. We coupled experimental screening with multivariate linear regression (MLR) analysis to gain greater insight regarding factors that influence the reaction scope. Furthermore, experiments paired with density functional theory (DFT) calculations provided key mechanistic insight into the nucleophilic substitution reactions at the sulfur(IV) center. The simplicity and short reaction times of our protocol facilitates the library syntheses of these key bioisosteres.