Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 418-422.DOI: 10.6023/cjoc201607032 Previous Articles     Next Articles



关志朋, 师瑶, 石炜, 陈浩   

  1. 华中农业大学理学院 武汉 430070
  • 收稿日期:2016-07-20 修回日期:2016-09-19 发布日期:2016-10-11
  • 通讯作者: 石炜
  • 基金资助:


Synthesis of Terminal Alkynes/Diynes through Deprotection of Acetone Protected Alkynes under Mild Conditions

Guan Zhipeng, Shi Yao, Shi Wei, Chen Hao   

  1. College of Science, Huazhong Agricultural University, Wuhan 430070
  • Received:2016-07-20 Revised:2016-09-19 Published:2016-10-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21202050), and the Natural Science Foundation of Hubei Province (No. 2014CFB930).

Terminal alkynes are important building blocks in organic synthesis. Acetone protected terminal alkynes are frequently used in alkyne synthesis and reactions, which could be easily prepared by Pd-catalyzed Sonogashira cross-coupling reactions between electrophiles and 2-methyl-3-butyn-2-ol. At present, the deprotection of the acetone protected terminal alkynes is generally carried out in reflux toluene in the presence of potassium hydroxide for hours. However, this procedure suffers from the harsh reaction conditions and its application has been limited. Here in the deprotection of acetones has been discussed, and various solvent, temperature, substrates were investigated to advance the procedure, and it is found that by employing 1,4-dioxane as solvent, this process can undergo smoothly at 60℃ with satisfying yields in 0.5~2 h in the presence of 2.0 equiv. KOH.

Key words: 1,4-dioxane, deprotection, terminal alkyne, 2-methyl-3-butyn-2-ol