《Electrochemical Synthesis of Hindered Primary and Secondary Amines via Proton-Coupled Electron Transfer》 was written by Lehnherr, Dan; Lam, Yu-hong; Nicastri, Michael C.; Liu, Jinchu; Newman, Justin A.; Regalado, Erik L.; DiRocco, Daniel A.; Rovis, Tomislav. SDS of cas: 100-48-1 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:
Accessing hindered amines, particularly primary amines α to a fully substituted carbon center, is synthetically challenging. We report an electrochem. method to access such hindered amines starting from benchtop-stable iminium salts and cyanoheteroarenes. A wide variety of substituted heterocycles (pyridine, pyrimidine, pyrazine, purine, azaindole) can be utilized in the cross-coupling reaction, including those substituted with a halide, trifluoromethyl, ester, amide, or ether group, a heterocycle, or an unprotected alc. or alkyne. Mechanistic insight based on DFT data, as well as cyclic voltammetry and NMR spectroscopy, suggests that a proton-coupled electron-transfer mechanism is operational as part of a hetero-biradical cross-coupling of α-amino radicals and radicals derived from cyanoheteroarenes. Safety: cyanide may be released as a byproduct leading to release of toxic HCN. In addition to this study using 4-Cyanopyridine, there are many other studies that have used 4-Cyanopyridine(cas: 100-48-1SDS of cas: 100-48-1) was used in this study.
4-Cyanopyridine(cas: 100-48-1) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. SDS of cas: 100-48-1