Recommanded Product: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (11bR)-N,N-Bis[(1R)-1-phenylethyl]dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, is researched, Molecular C36H30NO2P, CAS is 415918-91-1, about Regio- and Enantioselective N-Allylations of Imidazole, Benzimidazole, and Purine Heterocycles Catalyzed by Single-Component Metallacyclic Iridium Complexes. Author is Stanley, Levi M.; Hartwig, John F..
Highly regio- and enantioselective iridium-catalyzed N-allylations of benzimidazoles, imidazoles, and purines were developed. N-Allylated benzimidazoles and imidazoles were isolated in high yields (up to 97%) with high branched-to-linear selectivity (up to 99:1) and enantioselectivity (up to 98% ee) from the reactions of benzimidazole and imidazole nucleophiles with unsym. allylic carbonates in the presence of single component, ethylene-bound, metallacyclic iridium catalysts. N-Allylated purines were also obtained in high yields (up to 91%) with high N9/N7 selectivity (up to 96:4), high branched-to-linear selectivity (98:2), and high enantioselectivity (up to 98% ee) under similar conditions. Competition experiments between common amine nucleophiles and the heterocyclic nitrogen nucleophiles illustrated the effect of nucleophile pKa on the rate of the iridium-catalyzed N-allylation reactions. Kinetic studies on the allylation of benzimidazole catalyzed by metallacyclic iridium-phosphoramidite complexes, in combination with studies on the deactivation of these catalysts in the presence of heterocyclic nucleophiles, provided insight into the effects of the structures of the phosphoramidite ligands on the stability of the metallacyclic catalysts.
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