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Copper-catalyzed oxidative sulfenylation and alkylation of indolin-2-ones for direct construction of sulfur-substituted quaternary carbons
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2024-04-12 , DOI: 10.1039/d4qo00491d
Yun-Hao Zhang 1 , Yi-Nuo Wang 1 , Zi-Yu Liu 1 , Si-Han Zheng 2 , Guang-Lin Li 1 , Dexin Feng 3 , Da-Zhen Xu 1
Affiliation  

The selective functionalization of ubiquitous C(sp3)–H bonds for constructing complex molecules is a highly sought-after method in academia as well as the chemical industry. In particular, it is rather challenging to install two different kinds of substituent groups into one reaction site in a one-pot process. To aid in this effort, we have developed a one-pot reaction for the construction of S-substituted quaternary carbon centers starting from secondary C(sp3)–H substrates. A sulfenylation and alkylation procedure catalyzed by simple copper salts has been established. It provides a rapid access to C3-alkylated 3-thioxyindolin-2-ones from abundant feedstock chemicals and features operational simplicity, broad substrate scope and good functional group compatibility.

中文翻译:

铜催化二氢吲哚-2-酮的氧化磺酰化和烷基化直接构建硫取代的季碳

用于构建复杂分子的普遍存在的 C(sp 3 )–H 键的选择性功能化是学术界和化学工业中备受追捧的方法。特别是,在一锅法中将两种不同类型的取代基安装到一个反应位点是相当具有挑战性的。为了帮助实现这一目标,我们开发了一种一锅反应,用于从二级 C(sp 3 )–H 底物开始构建S取代的季碳中心。已经建立了由简单铜盐催化的磺基化和烷基化程序。它可以从丰富的原料化学品中快速获得C3-烷基化的3-硫氧基二氢吲哚-2-酮,并具有操作简单、底物范围广和良好的官能团兼容性的特点。
更新日期:2024-04-17
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