Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines was written by Turro, Raymond F.;Brandstatter, Marco;Reisman, Sarah E.. And the article was included in Angewandte Chemie, International Edition in 2022.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:
The preparation of heterobenzylic amines, e.g., I [R1 = H, 4-Cl, 5-F, 6-Me, etc.; R2 = i-Pr, n-Bu, t-Bu, cyclopropyl, cyclobutyl, (R)-PhCHMe; R3 = H, Me, R4 = PhCH2; R3 = H, R4 = 4-ClC6H4CH2, 2,6-Me2C6H3CH2, etc.; R3R4 = (CH2)2X(CH2)2; X = CH2, O, CO, NBoc], by a Ni-catalyzed reductive cross-coupling between heteroaryl imines, e.g., II, and C(sp3) electrophiles R3R4CHX1 (X1 = Cl, Br, I, phthalimidyloxycarbonyl) is reported. This umpolung-type alkylation proceeds under mild conditions, avoids the pre-generation of organometallic reagents, and exhibits good functional group tolerance. Mechanistic studies are consistent with the imine substrate acting as a redox-active ligand upon coordination to a low-valent Ni center. The resulting bis(2-imino)heterocycle·Ni complexes can engage in alkylation reactions with a variety of C(sp3) electrophiles, giving heterobenzylic amine products in good yields. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).
1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem