Huang Tian-Sih, Chen Chun-Lin, Tsai Ming-Hsuan, Chen Yu-Chi, Hsu Che-Sheng
Department of Chemistry, Fu Jen Catholic University, 510 Zhongzheng Road, Xinzhuang District, New Taipei City, 24205, Taiwan.
Chemistry. 2025 Feb 6;31(8):e202403947. doi: 10.1002/chem.202403947. Epub 2024 Nov 28.
Vinyl sulfones are valued for their unique chemical properties and bioactivity, but creating a wide range of different analogs remains a challenge. To address this limitation, we have developed a novel approach that facilitates the synthesis of polysubstituted vinyl sulfones. This method utilizes the dual functionality of NIS as a promoter that enables sulfonation and elimination in the synthesis of vinyl sulfones. We used the broad applicability, efficiency, selectivity, and functional group tolerance of this approach to synthesize more than 70 examples. Additionally, competition experiments have provided insights into the reactivity and selectivity of the transient sulfonyl radical towards various C-C multiple bonds. Herein, we describe using this mild protocol in the late-stage vinyl sulfonation of complex molecules to simplify the synthesis of specific targets and enable the modification of complex natural products and advanced materials.
乙烯基砜因其独特的化学性质和生物活性而备受重视，但合成多种不同的类似物仍然是一项挑战。为了解决这一限制，我们开发了一种新颖的方法，该方法有助于多取代乙烯基砜的合成。此方法利用NIS作为促进剂的双重功能，在乙烯基砜的合成中实现磺化和消除反应。我们利用该方法的广泛适用性、效率、选择性和官能团耐受性合成了70多个实例。此外，竞争实验为瞬态磺酰基自由基对各种碳 - 碳多重键的反应性和选择性提供了深入了解。在此，我们描述了在复杂分子的后期乙烯基磺化中使用这种温和的方案，以简化特定目标的合成，并实现复杂天然产物和先进材料的修饰。
