In 2022,Turro, Raymond F.; Brandstatter, Marco; Reisman, Sarah E. published an article in Angewandte Chemie, International Edition. The title of the article was 《Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines》.Computed Properties of C5H9BrO The author mentioned the following in the article:
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. After reading the article, we found that the author used 4-Bromotetrahydropyran(cas: 25637-16-5Computed Properties of C5H9BrO)
4-Bromotetrahydropyran(cas: 25637-16-5) is often used as reactant for: nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents, preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans; preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes.Computed Properties of C5H9BrO
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics