1-Alkali-metal-2-alkyl-1,2-dihydropyridines: Soluble Hydride Surrogates for Catalytic Dehydrogenative Coupling and Hydroboration Applications.
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ABSTRACT: Equipped with excellent hydrocarbon solubility, the lithium hydride surrogate 1-lithium-2-tert-butyl-1,2-dihydropyridine (1tLi) functions as a precatalyst to convert Me2 NH⋅BH3 to [NMe2 BH2 ]2 (89 % conversion) under competitive conditions (2.5 mol %, 60 h, 80 °C, toluene solvent) to that of previously reported LiN(SiMe3 )2 . Sodium and potassium dihydropyridine congeners produce similar high yields of [NMe2 BH2 ]2 but require longer times. Switching the solvent to pyridine induces a remarkable change in the dehydrocoupling product ratio, with (NMe2 )2 BH favoured over [NMe2 BH2 ]2 (e.g., 94 %:2 % for 1tLi). Demonstrating its v
SUBMITTER: McLellan R
PROVIDER: S-EPMC5820744 | biostudies-literature | 2017 Nov
REPOSITORIES: biostudies-literature
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