有机化学 ›› 2015, Vol. 35 ›› Issue (7): 1500-1505.DOI: 10.6023/cjoc201501036 上一篇    下一篇

研究论文

三氟甲磺酸催化环丙基醇与磺酰胺的串联反应高效合成四氢吡咯衍生物

张小祥, 孙小萍, 饶卫东   

  1. 南京林业大学化工学院 江苏省生物质绿色燃料与化学品重点实验室 南京 210037
  • 收稿日期:2015-01-27 修回日期:2015-03-06 出版日期:2015-07-25 发布日期:2015-03-17
  • 通讯作者: 张小祥, 饶卫东 E-mail:s070038@hotmail.com;wdrao15@163.com
  • 基金资助:

    国家自然科学青年基金(No. 21302096)、江苏省自然科学青年基金(No. BK20130962)、江苏高校优势学科建设工程资助项目.

Triflic Acid-Catalyzed Tandem Reactions of Cyclopropyl Alcohols with Sulfonamides for the Synthesis of Pyrrolidines

Zhang Xiaoxiang, Sun Xiaoping, Rao Weidong   

  1. College of Chemical Engineering, Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing Forestry University, Nanjing 210037
  • Received:2015-01-27 Revised:2015-03-06 Online:2015-07-25 Published:2015-03-17
  • Supported by:

    Project supported by the Young National Natural Science Foundation of China (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (No. BK20130962) and the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions.

三氟甲磺酸(TfOH)可以用于催化取代环丙基醇与磺酰胺经分子间串联合成四氢吡咯衍生物的反应. 在100 ℃以及10 mol% TfOH作为催化剂作用下, 可获得产率为16%~83%的四氢吡咯衍生物目标产物. 该反应在优化条件下能够适用于各种类型的取代环丙基醇和磺酰胺类化合物, 例如芳环上带有吸电子基团、给电子基团和具有位阻效应的基团的环丙基醇, 含有吸电子以及给电子基团的磺酰胺类化合物. 相对便宜、容易获得的TfOH是一种有效的替代金属催化合成四氢吡咯的试剂.

关键词: TfOH催化, 环丙基醇, 磺酰胺, 串联反应, 四氢吡咯衍生物

Intermolecular tandem reactions of substituted cyclopropyl alcohols with sulfonamides for the synthesis of pyrrolidines can be catalyzed by triflic acid (TfOH). The desired pyrrolidines were provided in yields of 16%~83% with 10 mol% catalyst loadings at 100 ℃. A variety of cyclopropyl alcohols, such as the electron-withdrawing, electron-donating and bulkyl groups on aromatics, and sulfonamide with electron-withdrawing, and electron-donating substituents, could be tolerated under the optimized reaction conditions. An inexpensive and commercially available triflic acid reagent has been shown efficient for the synthesis of pyrrolidines, which is an alternative to metal-catalyzed reactions.

Key words: TfOH-catalyzed, cyclopropyl alcohols, sulfonamides, tandem reactions, pyrrolidines