4.8 Article

Manganese-Catalyzed Multicomponent Synthesis of Pyrimidines from Alcohols and Amidines

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 6, Pages 1663-1666

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611318

Keywords

borrowing-hydrogen reactions; dehydrogenative coupling; maganese; pincer complexes; pyrimidines

Funding

  1. Deutsche Forschungsgemeinschaft, DFG [SFB 840]

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The development of catalytic reactions for synthesizing different compounds from alcohols to save fossil carbon feedstock and reduce CO2 emissions is of high importance. Replacing rare noble metals with abundantly available 3d metals is equally important. We report a manganese-complex-catalyzed multicomponent synthesis of pyrimidines from amidines and up to three alcohols. Our reaction proceeds through condensation and dehydrogenation steps, permitting selective C-C and C-N bond formations. -Alkylation reactions are used to multiply alkylate secondary alcohols with two different primary alcohols to synthesize fully substituted pyrimidines in a one-pot process. Our PN5P-Mn-pincer complexes efficiently catalyze this multicomponent process. A comparison of our manganese catalysts with related cobalt catalysts indicates that manganese shows a reactivity similar to that of iridium but not cobalt. This analogy could be used to develop further (de)hydrogenation reactions with manganese complexes.

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