Synthesis of Fluoroalkyl Sulfides via Additive-Free Hydrothiolation and Sequential Functionalization Reactions
Synthesis of Fluoroalkyl Sulfides via Additive-Free Hydrothiolation and Sequential Functionalization Reactions
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通过无添加剂硫氢化和顺序官能化反应合成氟代烷基硫醚
DOI：
10.1021/acs.joc.1c00361
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Ogoshi Sensuke
中科院分区：
文献类型：
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作者：
Sunagawa Denise E.;Ishida Naoyoshi;Iwamoto Hiroaki;Ohashi Masato;Fruit Corinne;Ogoshi Sensuke
发展了一种模块化合成方法，包括氢硫醇化、硅烷化和氟烷基化，用于构建高度官能化的氟烷基硫醚。非质子极性溶剂的使用使得能够无添加剂地化学选择性氢硫醇化三氟氯乙烯和六氟丙烯与各种硫醇。逐步官能化反应将氢硫醇化的中间体高效地转化为三乙基硫醚。该方法避免了使用环境污染物哈龙-2402，哈龙-2402在报道的合成路线中被用作结构单元。
A modular synthetic method, involving a hydrothiolation, silylation, and fluoroalkylation, for the construction of highly functionalized fluoroalkyl sulfides has been developed. The use of aprotic polar solvents enables the additive-free chemoselective hydrothiolation of tetrafluoroethylene, trifluorochloroethylene, and hexafluoropropene with various thiols. The stepwise functionalization reactions convert the hydrothiolated intermediates into the tetrafluoroethyl sulfides in high efficiency. The method avoids the use of the environmental pollutant Halon-2402, which was employed as a building block in a reported synthetic route.