One-pot synthesis of selenocarbamates from isocyanates and diselenides using the Zn/AlCl3 system

Click Reaction of Selenols with Isocyanates: Rapid Access to Selenocarbamates as Peroxide‐Switchable Reservoir of Thiol‐Peroxidase‐Like Catalysts

“…GC-MS was performed on a Varian CP 3800/Saturn 2200 instrument. 1 H and 13 C NMR spectra were recorded in CDCl 3 using Varian Mercury 400 and Bruker 400 Ultrashield spectrometers operating at 400 MHz for 1 H and 100 MHz for 13 C. 77 Se NMR spectra were recorded using a Bruker 400 Ultrashield spectrometer, operating at 76 MHz. NMR signals were referenced to nondeuterated residual solvent signals (7.26 ppm for 1 H, 77.0 ppm for 13 C).…”

“…However, in spite of their wide application, only a few methodologies have been reported for the preparation of selenocarbamates. These approaches generally rely on the reactivity of isocyanates with selenium‐centered nucleophiles such as selenocarboxylic acids [12] or selenolates, generated by means of reductive cleavage of diselenides with Zn/AlCl 3 [13] . N ‐Alkyl‐ Se ‐alkylselenocarbamates can be prepared from isocyanates and haloalkanes by using LiAlHSeH as the selenating reagent [14] .…”

“…These approaches generally rely on the reactivity of isocyanates with seleniumcentered nucleophiles such as selenocarboxylic acids [12] or selenolates, generated by means of reductive cleavage of diselenides with Zn/AlCl 3 . [13] N-Alkyl-Sealkylselenocarbamates can be prepared from isocyanates and haloalkanes by using LiAlHSeH as the selenating reagent. [14] Other methods involve the reaction of amines and carbon monoxide with elemental selenium, followed by treatment with alkyl halides, [15] the reduction of diselenides with lithium triethylborohydride followed by the reaction with diethyl carbamoyl chloride, [16] as well as the reductive cleavage and subsequent alkylation of bis(N,N-dimethylcarbamoyl)diselenide.…”