A convenient, transition metal-free synthesis of difluoromethyl selenoethers from organic selenocyanates and TMSCF2H

作者：Dong, Tao; Nie, Jing; Zhang, Cheng-Pan^*

来源：Tetrahedron, 2018, 74(39): 5642-5649.

DOI：10.1016/j.tet.2018.08.001

• Difluoromethyl selenoether
• Transition metal-free
• Selenocyanate
• Difluoromethylselenol
• Difluoromethylation

An efficient and transition metal-free method for the synthesis of aryl or alkyl difluoromethyl selenides (RSeCF2H) from the corresponding selenocyanates (RSeCN) and TMSCF2H/t-BuOK is described. The reaction performed in THE at 0 degrees C for 24 h or at room temperature for 6 h supplied a series of RSeCF2H in good to high yields. The successful preparation of difluoromethylselenolated sulfadimethoxine derivative and the scaled-up synthesis of 1-benzyl-5-((difluoromethyl)selanyl)indoline, as examples, suggested good practicability of this method. Advantages of the reaction include mild reaction conditions, good functional group tolerance, a wide range of substrates, and high efficiency. This protocol offered a number of novel difluoromethyl selenoethers, which would accelerate use of such compounds in the areas of life science.

• 出版日期2018-9-27
• 单位武汉理工大学