碘化四丁基铵促进的以磺酰氯为硫烯基化试剂的氧化吲哚硫醇化反应

Tetrabutylammonium Iodide-Promoted Thiolation of Oxindoles Using Sulfonyl Chlorides as Sulfenylation Reagents.

作者信息

Zhao Xia, Wei Aoqi, Lu Xiaoyu, Lu Kui

机构信息

College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key laboratory of Inorganic-organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Normal University, Tianjin 300387, China.

College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, China.

出版信息

Molecules. 2017 Aug 1;22(8):1208. doi: 10.3390/molecules22081208.

DOI:10.3390/molecules22081208

PMID:28763049

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6152007/

Abstract

3-Sulfanyloxindoles were synthesised by triphenylphosphine-mediated transition-metal-free thiolation of oxindoles using sulfonyl chlorides as sulfenylation reagents. The above reaction was promoted by iodide anions, which was ascribed to the in situ conversion of sulfenyl chlorides into the more reactive sulfenyl iodides. Moreover, the thiolation of 3-aryloxindoles was facilitated by bases. The use of a transition-metal-free protocol, readily available reagents, and mild reaction conditions make this protocol more practical for preparing 3-sulfanyloxindoles than traditional methods.

摘要

以磺酰氯作为硫烯化试剂，通过三苯基膦介导的氧化吲哚无过渡金属硫醇化反应合成了3-硫代氧化吲哚。上述反应由碘离子促进，这归因于硫烯基氯原位转化为反应活性更高的硫烯基碘。此外，碱促进了3-芳基氧化吲哚的硫醇化反应。与传统方法相比，该无过渡金属方案、易于获得的试剂和温和的反应条件使得该方案在制备3-硫代氧化吲哚方面更具实用性。