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Synthesis of sulfonyl‐containing spiro[5,5]trienones from sodium metabisulfite
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2024-05-11 , DOI: 10.1002/adsc.202400345
Wei Xiao 1 , Zhimei Tang 2 , Fu-Sheng He 2 , Jie Wu 2
Affiliation  

An efficient three‐component reaction of biaryl ynones, sodium metabisulfite and aryldiazonium tetrafluoroborates is developed. The reaction occurs at room temperature without any additives, thus offering a sustainable approach to access sulfonyl‐containing spiro[5,5]trienones. This protocol features mild conditions, broad substrate scope and high functional group compatibility, furnishing the target products in moderate to good yields. Mechanistic studies indicate that the reaction undergoes a 6‐exo‐trig dearomative spirocyclization process which is initated by an aryl radical with the insertion of sulfur dioxide.

中文翻译:

焦亚硫酸钠合成含磺酰基螺[5,5]三烯酮

开发了联芳基炔酮、焦亚硫酸钠和芳基重氮四氟硼酸盐的有效三组分反应。该反应在室温下发生,无需任何添加剂,从而提供了一种可持续的方法来获取含磺酰基的螺[5,5]三烯酮。该方案具有条件温和、底物范围广、官能团相容性高等特点,目标产物收率中等至良好。机理研究表明,该反应经历了 6-exo-trig 脱芳香螺环化过程,该过程是由芳基自由基插入二氧化硫引发的。
更新日期:2024-05-11
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