50983-89-6Relevant academic research and scientific papers
Metal-Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium
Huang, Xiao-Bo,Liu, Miao-Chang,Wu, Hua-Yue,Zhang, Xue,Zhou, Yun-Bing
supporting information, p. 944 - 948 (2020/12/18)
This work reports a green method for the synthesis of aryl selenocyanates via a three-component reaction of arylboronic acids, Se powder, and trimethylsilyl cyanide (TMSCN) under metal-free and additive-free conditions. Remarkably, TMSCN acts as not only the substrate, but also the catalyst. Various selenaheterocycles can be also accessed with a catalytic amount of TMSCN.
Metal-Free ipso -Selenocyanation of Arylboronic Acids Using Malononitrile and Selenium Dioxide
Broggi, Julie,Kosso, Anne Roly Obah,Redon, Sébastien,Vanelle, Patrice
supporting information, p. 3758 - 3764 (2019/09/30)
The first ipso -selenocyanation of arylboronic acids is achieved using selenium dioxide and malononitrile under mild conditions. The reaction is successful even without metal or base in DMSO. The major advantages of this new method are an easy set-up, excellent yields, and the use of odorless and inexpensive selenium reagents. Basic conditions subsequently afford new access to diaryldiselenides in good yields without isolating the organoselenocyanate intermediates.
Metal-free synthesis of unsymmetrical organoselenides and selenoglycosides
Guan, Yong,Townsend, Steven D.
supporting information, p. 5252 - 5255 (2017/11/06)
A one-pot, metal-free procedure has been developed to synthesize unsymmetrical organoselenides. In the first step of the reaction, arylation of potassium selenocyanate (KSeCN) with an iodonium reagent proceeds in the absence of a metal catalyst to produce
Reaction of Areneselenyl Chlorides and alkenes. An example of Nucleophilic Displacement at Bivalent Selenium
Schmid, George H.,Garratt, Dennis G.
, p. 4169 - 4172 (2007/10/02)
The effect of substituents in the phenyl ring of both the electrophile and the alkene has been studied in the reaction of areneselenyl chlorides and (E)- and (Z)-1-phenylpropenes.Electron-donating groups in both phenyl rings enhance the rate of reaction.Viewing this reaction as a nucleophilic displacement at bivalent selenium leads to a model that allows the possibility of reaction by a continuum of mechanisms.These mechanisms differ only in the relative amounts of C-Se bond making and Se-Cl bond breaking in the rate-determining transition state.From our data, it is concluded that C-Se bond making lags behind Se-Cl bond breaking in the rate determining transition state.
