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.Computed Properties of C9H11Br 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, 2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7Computed Properties of C9H11Br).
2-(Bromomethyl)-1,3-dimethylbenzene (cas: 83902-02-7) belongs to organobromine compounds. Many of the organo bromine compounds are relatively nonpolar. Bromine is more electronegative than carbon (2.8 vs 2.5) and hence the carbon in a carbonbromine bond is electrophilic in nature. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Computed Properties of C9H11Br
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary