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Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation
Organic Letters ( IF 5.2 ) Pub Date : 2021-12-06 , DOI: 10.1021/acs.orglett.1c03813
Haonan Xiang 1 , Jie Liu 1 , Jieping Wang 1 , Lvqi Jiang 1 , Wenbin Yi 1, 2
Affiliation  

A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barrier in the first step of deoxygenation. The mild deoxygenation process enables the reduction of a wide range of functionalized sulfonyl chlorides as well as sulfonic anhydrides. The novel method represents an operationally simple protocol using readily available reagents and exhibits broad functional group tolerance.

中文翻译:

方酸在溴催化磺酰基衍生物脱氧中的协同作用:在亲电(氟烷基)亚磺酰基化中的机理研究和合成应用

报道了一种通过协同 CTAB 和方酸促进的磺酰基衍生物脱氧对亲核试剂进行亲电(氟烷基)亚磺酰化的方法。机理研究表明,方酸在脱氧的第一步中显着降低了能量屏障。温和的脱氧过程能够还原多种功能化磺酰氯以及磺酸酐。这种新方法代表了一种使用现成试剂的操作简单的协议,并表现出广泛的官能团耐受性。
更新日期:2022-01-14
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