期刊
TETRAHEDRON
卷 74, 期 39, 页码 5642-5649出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.08.001
关键词
Difluoromethyl selenoether; Transition metal-free; Selenocyanate; Difluoromethylselenol; Difluoromethylation
资金
- Wuhan University of Technology
- National Natural Science Foundation of China [21602165]
- Department of Education of Hubei Province (China)
- Hundred Talent Program of Hubei Province
- Wuhan Youth Chen-Guang Project [2016070204010113]
- Wuhan University of Technology [2017-YS-082]
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. (C) 2018 Elsevier Ltd. All rights reserved.
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