有机化学 ›› 2020, Vol. 40 ›› Issue (10): 3300-3306.DOI: 10.6023/cjoc202005011 上一篇    下一篇

研究论文

铜(I)促进的3-重氮吲哚-2-亚胺与AgSCF3的三氟甲硫基化反应:3-三氟甲硫基-2-氨基吲哚的合成

郎勃, Muhammad Suleman, 吕萍, 王彦广   

  1. 浙江大学化学系 杭州 310027
  • 收稿日期:2020-05-05 修回日期:2020-06-16 发布日期:2020-08-01
  • 通讯作者: 吕萍, 王彦广 E-mail:pinglu@zju.edu.cn;orgwyg@zju.edu.cn
  • 基金资助:
    国家自然科学基金(Nos.21772169,21632003)资助项目.

Copper(I)-Promoted Trifluoromethylthiolation of 3-Diazoindolin-2-imines with AgSCF3: Synthesis of 3-((Trifluoromethyl)thio)-2-aminoindoles

Lang Bo, Suleman Muhammad, Lu Ping, Wang Yanguang   

  1. Department of Chemistry, Zhejiang University, Hangzhou 310027
  • Received:2020-05-05 Revised:2020-06-16 Published:2020-08-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21772169, 21632003).

报道了一种通过铜(I)促进的3-重氮吲哚-2-亚胺与AgSCF3的三氟甲硫基化反应,合成3-三氟甲硫基-2-氨基吲哚类化合物的简洁、高效新方法,其主要特征包括底物范围广,铜(I)催化剂廉价,重氮原料和三氟甲硫基化试剂容易获得,反应条件温和且时间短;此外,适量的水能够促进这一反应.

关键词: 重氮化合物, 金属卡宾, 三氟甲硫基化, 铜催化, 吲哚, 杂环

A facile and efficient method for the synthesis of novel 3-((trifluoromethyl)thio)-2-aminoindoles through copper (I)-promoted trifluoromethylthiolation of 3-diazoindolin-2-imines with AgSCF3 is reported. This methodology features a broad substrate scope of diazo compounds, economical copper(I) catalyst, readily available and stable diazo materials and trifluoromethylthiolating reagent, mild reaction conditions, short reaction time and water assisted higher yields.

Key words: diazo compounds, metal carbenes, trifluoromethylthiolation, copper catalysis, indoles, heterocycles