高价碘（III）试剂介导的中断Pummerer反应：RSCl的原位形成及其在3-亚磺酰化吲哚合成中的应用
An Interrupted Pummerer Reaction Mediated by a Hypervalent Iodine(III) Reagent: In Situ Formation of RSCl and Its Application for the Synthesis of 3-Sulfenylated Indoles.
作者信息
Zhang Beibei, Li Xuemin, Li Xiaoxian, Yu Zhenyang, Zhao Bingyue, Wang Xiaofan, Du Yunfei, Zhao Kang
机构信息
Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
State Key Laboratory of Microbial Technology, Institute of Microbial Technology, Shandong University, Qingdao 266237, China.
出版信息
J Org Chem. 2021 Dec 3;86(23):17274-17281. doi: 10.1021/acs.joc.1c02404. Epub 2021 Nov 22.
An interrupted Pummerer reaction of PhICl and sulfoxides was found to in situ generate reactive organosulfenyl chloride, which enabled the intramolecular electrophilic cyclization of 2-alkynylanilines, generating 3-sulfenylated indole with a good to excellent yield under metal-free conditions. One striking feature of the approach is that sulfoxide regeneration can be realized via the oxidation of the formed sulfides by the generated hypervalent iodine species.
发现PhICl与亚砜的间断Pummerer反应能原位生成活性有机亚磺酰氯，这使得2-炔基苯胺能够进行分子内亲电环化反应，在无金属条件下以良好至优异的产率生成3-亚磺酰化吲哚。该方法的一个显著特点是，通过生成的高价碘物种氧化生成的硫化物，可以实现亚砜的再生。
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