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• W2082403126 abstract "Highly regio- and enantioselective iridium-catalyzed N-allylations of benzimidazoles, imidazoles, and purines have been 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 unsymmetrical 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. The reactions encompass a range of benzimidazole, imidazole, and purine nucleophiles, as well as a variety of unsymmetrical aryl, heteroaryl, and aliphatic allylic carbonates. Competition experiments between common amine nucleophiles and the heterocyclic nitrogen nucleophiles studied in this work illustrate the effect of nucleophile pKa on the rate of 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, provide insight into the effects of the structures of the phosphoramidite ligands on the stability of the metallacyclic catalysts. The data obtained from these studies have led to the development of N-allylations of benzimidazoles and imidazoles in the absence of an exogenous base." @default.
• W2082403126 created "2016-06-24" @default.
• W2082403126 creator A5044446269 @default.
• W2082403126 creator A5088865204 @default.
• W2082403126 date "2009-05-29" @default.
• W2082403126 modified "2023-10-02" @default.
• W2082403126 title "Regio- and Enantioselective <i>N</i>-Allylations of Imidazole, Benzimidazole, and Purine Heterocycles Catalyzed by Single-Component Metallacyclic Iridium Complexes" @default.
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• W2082403126 doi "https://doi.org/10.1021/ja902243s" @default.
• W2082403126 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2841989" @default.
• W2082403126 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19480431" @default.
• W2082403126 hasPublicationYear "2009" @default.
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