101220-61-5Relevant articles and documents
A convenient, transition metal-free synthesis of difluoromethyl selenoethers from organic selenocyanates and TMSCF2H
Dong, Tao,Nie, Jing,Zhang, Cheng-Pan
, p. 5642 - 5649 (2018/08/22)
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 THF at 0 °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.
S-, N-, and Se-difluoromethylation using sodium chlorodifluoroacetate
Mehta, Vaibhav P.,Greaney, Michael F.
supporting information, p. 5036 - 5039 (2013/10/22)
A simple protocol for the difluoromethylation of thiols is reported using chlorodifluoroacetate as the difluoromethylating agent. This cheap reagent undergoes smooth decarboxylation at 95 C to afford difluorocarbene, which can be trapped with a variety of aromatic and heteroaromatic thiols. The reaction is also effective for the difluoromethylation of heterocyclic nitrogen compounds and phenylselenol.
Reaction of Difluoromethyl Phenyl Selenoxide with Acetic Anhydride. A Route to Difluoro(phenylseleno)methylation of Ethers
Uneyama, Kenji,Maeda, Kazuhiro,Tokunaga, Yukio,Itano, Nobuaki
, p. 370 - 375 (2007/10/02)
Difluoromethyl phenyl selenoxide (2) has been prepared and allowed to react with acetic anhydride in the presence of cyclic ethers and sulfides.Difluorophenylselenomethylation occurred smoothly on reacting 2 with Ac2O in refluxing dichloromethane to give ω-alkyl acetates 4 in 34-87percent yields.A sequential reaction of Pummerer type rearrangement, difluorocarbene formation, electrophilic addition of the carbene to oxygen of ethers leading to oxonium ylide, and trapping with phenylselenyl acetate is proposed.
