Decarboxylation functionalization of carboxylic acids has evolved to valuable synthetic methods because of the structural diversity of carboxylic acids and their utility in drug discovery as directing groups for C–H activation. Although transition-metal-catalyzed decarboxylation is one of the most common methods, it typically requires complex operations and additives within a limited substrate scope. In this study, we show that the use of a palladium-catalyzed system together with sulfuryl fluoride can readily effect decarboxylative dehydrogenation and decarboxylative cross-coupling of various alkyl and aryl carboxylic acids. Based on mechanistic studies including DFT calculations, a detailed catalytic cycle is presented in which rapid generation of an acyl fluoride from the reaction of SO₂F₂ with a carboxylic acid is critical for initiating catalysis. The versatility of a new mediator platform has been demonstrated with a diverse range of substrates and applications.

中文翻译：

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使用硫酰氟对羧酸进行脱羧官能化的有效平台：Pd 催化的烷烃羧酸脱羧脱氢和芳烃羧酸的脱羧交叉偶联


由于羧酸的结构多样性及其在药物发现中作为 C-H 活化导向基团的实用性，羧酸的脱羧功能化已发展成为有价值的合成方法。尽管过渡金属催化脱羧是最常见的方法之一，但它通常需要在有限的底物范围内进行复杂的操作和添加剂。在这项研究中，我们表明，使用钯催化体系与硫酰氟一起可以很容易地实现各种烷基和芳基羧酸的脱羧脱氢和脱羧交叉偶联。基于包括 DFT 计算在内的机理研究，提出了详细的催化循环，其中 SO ₂ F ₂ 与羧酸反应快速生成酰基氟对于引发催化。新介体平台的多功能性已通过各种底物和应用得到证明。