2769-30-4Relevant articles and documents
Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions
Goljani, Hamed,Tavakkoli, Zahra,Sadatnabi, Ali,Nematollahi, Davood
supporting information, p. 5920 - 5924 (2020/08/12)
The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.
Iron-Catalyzed Decarboxylation of Trifluoroacetate and Its Application to the Synthesis of Trifluoromethyl Thioethers
Exner, Benjamin,Bayarmagnai, Bilguun,Jia, Fan,Goossen, Lukas J.
supporting information, p. 17220 - 17223 (2016/01/25)
Nucleophilic CF3 has been generated by decarboxylation of potassium trifluoroacetate, arguably the most easy-to-handle, inexpensive, and sustainable source of trifluoromethyl groups. Simple iron(II) chloride catalyzes the decarboxylation as well as a subsequent trifluoromethylation of organothiocyanates, resulting in a straightforward synthesis of trifluoromethyl thioethers. The KCN byproduct is absorbed by iron(II) with formation of nontoxic potassium hexacyanoferrate. An analogous trifluoromethylation of aldehydes with trifluoroacetate underlines the synthetic potential of such iron-catalyzed decarboxylative trifluoromethylations.
Copper-catalyzed cyanation of disulfides by azobisisobutyronitrile leading to thiocyanates
Teng, Fan,Yu, Jin-Tao,Yang, Haitao,Jiang, Yan,Cheng, Jiang
supporting information, p. 12139 - 12141 (2014/12/11)
The copper-catalyzed cyanation of disulfides by azobisisobutyronitrile (AIBN) was developed, leading to thiocyanates in moderate to good yields. This procedure tolerates a series of functional groups, such as chloro, nitro, methyl and methoxycarbonyl in the phenyl ring of disulfides. Notably, it enables the use of two ArS units in (ArS)2. CuI was found to be essential for the in situ formation of cyanide anions. This journal is
Improved procedure to aryl thiocyanates: A new synthetic application of dry arenediazonium o-benzenedisulfonimides
Barbero,Degani,Diulgheroff,Dughera,Fochi
, p. 585 - 590 (2007/10/03)
Aryl thiocyanates 3 (22 examples) were easily prepared by reaction of dry arenediazonium o-benzenedisulfonimides 1 and sodium thiocyanate (2) in anhydrous acetonitrile at room temperature (20-25 °C) in the presence of copper powder (Procedure A) and at 50 °C or room temperature without the metal catalyst (Procedure B). The yields were from very good to excellent in Procedure A (average yield = 83%), and from modest to excellent in Procedure B (average yield = 63%). In comparison with the thiocyanod-ediazoniation carried out under traditional Sandmeyer-type conditions, the yields of 3 were higher and the isothiocyanate isomers were formed only in traces. Moreover, the results obtained in the absence of copper confirm the role of the anion of salts 1 as an electron transfer agent.
Aromatic Thiocyanation using Supported Copper(I) Thiocyanate
Clark, James H.,Jones, Craig W.,Duke, Catherine V. A.,Miller, Jack M.
, p. 81 - 82 (2007/10/02)
Charcoal Supported copper(I) thiocyanate can be used to convert bromo- and iodo-benzenes into phenyl thiocyanates with no contamination from phenyl isothiocyanates.
NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 23. DIETHYL PHOSPHOROCYANIDATE(DEPC): A USEFUL REAGENT FOR AN UNPRECEDENTED TRANSFORMATION OF SULFINIC ACIDS TO THIOCYANATES
Harusawa, Shinya,Shioiri, Takayuki
, p. 447 - 448 (2007/10/02)
Diethyl phosphorocyanidate(DEPC) can be efficiently used for a simple, one-step transformation of sulfinic acids to thiocyanates.
