Cu(OTf)2-mediated acylation and direct N-transacylation of sulfonamides

IF 2.1 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Sulfur Chemistry Pub Date : 2024-09-02 DOI:10.1080/17415993.2024.2378777

Juan Tian , Mengyun Chen , Junshuo Chen , Chengya Shao , Kangkang Yu , Yunfeng Liu , Dayong Sang

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Abstract

Metal triflate-catalyzed acylation of sulfonamides and direct transacylation of N-acylsulfonamides have been investigated. The acylation of sulfonamides proceeds efficiently in the presence of a catalytic amount of Cu(OTf)₂ (0.001 equiv) using either carboxylic anhydrides or acyl chlorides as the acylating agents. Alternative catalysts suitable for this transformation include Al(OTf)₃, Fe(OTf)₃, Ga(OTf)₃, In(OTf)₃, and Er(OTf)₃. In the presence of Cu(OTf)₂ (0.2 equiv), N-acylsulfonamides undergo direct transacylation in excess acyl chlorides (10 equiv) to furnish new N-acylsulfonamides through exchange of N-acyl groups. Ga(OTf)₃, Fe(OTf)₃, and In(OTf)₃ are similarly reactive in catalyzing such transacylation transformations. The reaction conditions are mild and operationally convenient. A variety of functional groups including halogeno, keto, nitro, cyano, ether, and carboxylic ester are tolerated, providing the corresponding monoacylated N-acylsulfonamides in good to excellent yields.

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Cu(OTf) 2 介导的磺酰胺酰化反应和直接 N-反式酰化反应

研究了金属三盐酸盐催化的磺酰胺酰化反应和 N-酰基磺酰胺的直接反酰化反应。使用羧酸酐或酰基氯作为酰化剂，在催化量为 Cu(OTf)2 （0.001 等量）的情况下，磺酰胺的酰化反应可以高效进行。在 Cu(OTf)2（0.2 等量）存在下，N-酰基磺酰胺在过量酰基氯（10 等量）中直接发生酰化反应，通过交换 N-酰基生成新的 N-酰基磺酰胺。Ga(OTf)3、Fe(OTf)3 和 In(OTf)3 在催化这种反酰化转化时也具有类似的反应活性。反应条件温和，操作方便。可容忍包括卤代、酮基、硝基、氰基、醚基和羧酸酯在内的各种官能团，以良好至极佳的收率提供相应的单酰化 N- 烷基磺酰胺。

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来源期刊

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.