Nicastri, Michael C.’s team published research in Journal of the American Chemical Society in 142 | CAS: 1016841-67-0

Journal of the American Chemical Society published new progress about 1016841-67-0. 1016841-67-0 belongs to imidazoles-derivatives, auxiliary class Imidazoles, name is 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile, and the molecular formula is C10H8N4, Application of 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile.

Nicastri, Michael C. published the artcileSynthesis of Sterically Hindered Primary Amines by Concurrent Tandem Photoredox Catalysis, Application of 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile, the publication is Journal of the American Chemical Society (2020), 142(2), 987-998, database is CAplus and MEDLINE.

Primary amines are an important structural motif in active pharmaceutical ingredients (APIs) and intermediates thereof, as well as members of ligand libraries for either biol. or catalytic applications. Many chem. methodologies exist for amine synthesis, but the direct synthesis of primary amines with a fully substituted α carbon center is an underdeveloped area. We report a method which utilizes photoredox catalysis to couple readily available O-benzoyl oximes with cyanoarenes to synthesize primary amines with fully substituted α-carbons. We also demonstrate that this method enables the synthesis of amines with α-trifluoromethyl functionality. Based on exptl. and computational results, we propose a mechanism where the photocatalyst engages in concurrent tandem catalysis by reacting with the oxime as a triplet sensitizer in the first catalytic cycle and a reductant toward the cyanoarene in the second catalytic cycle to achieve the synthesis of hindered primary amines via heterocoupling of radicals from readily available oximes.

Journal of the American Chemical Society published new progress about 1016841-67-0. 1016841-67-0 belongs to imidazoles-derivatives, auxiliary class Imidazoles, name is 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile, and the molecular formula is C10H8N4, Application of 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem

Lehnherr, Dan’s team published research in Journal of the American Chemical Society in 142 | CAS: 1016841-67-0

Journal of the American Chemical Society published new progress about 1016841-67-0. 1016841-67-0 belongs to imidazoles-derivatives, auxiliary class Imidazoles, name is 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile, and the molecular formula is C10H8N4, Application of 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile.

Lehnherr, Dan published the artcileElectrochemical Synthesis of Hindered Primary and Secondary Amines via Proton-Coupled Electron Transfer, Application of 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile, the publication is Journal of the American Chemical Society (2020), 142(1), 468-478, database is CAplus and MEDLINE.

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.

Journal of the American Chemical Society published new progress about 1016841-67-0. 1016841-67-0 belongs to imidazoles-derivatives, auxiliary class Imidazoles, name is 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile, and the molecular formula is C10H8N4, Application of 2-(2-Methyl-1H-imidazol-1-yl)pyridine-4-carbonitrile.

Referemce:
https://en.wikipedia.org/wiki/Imidazole,
Imidazole | C3H4N2 – PubChem