二氟卡宾
化学
硫代氨基甲酸酯类
重氮甲烷
催化作用
分解
硫黄
有机化学
药物化学
组合化学
作者
Kohei Fuchibe,Masaki Bando,Ryo Takayama,Junji Ichikawa
标识
DOI:10.1016/j.jfluchem.2014.08.013
摘要
Upon treatment with trimethylsilyl 2,2-difluoro-2-fluorosulfonylacetate (TFDA) and a catalytic amount of N,N,N′,N′-tetramethyl-1,8-diaminonaphthalene, secondary thioamides and thiocarbamates undergo selective difluoromethylation on the sulfur atom to give S-difluoromethyl thioimidates and thioiminocarbonates in good yields, respectively. This is the first report on the synthesis of acyclic difluoromethyl thioimidates and thioiminocarbonates. The key for S-difluoromethylation is the organocatalytic generation of difluorocarbene (:CF2) under mild conditions, which prevents decomposition of the substrates. This process provides an efficient approach to pharmaceuticals and agrochemicals bearing a difluoromethylsulfanyl group, starting from widely available thiocarbonyl compounds.
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