Catalytic insertion of nitrenes into B-H bonds
Nikita M Ankudinov1, Nikita V Alexeev1,2, Evgeniya S Podyacheva1,3
1A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences 28 Vavilova Str. Moscow 119334 Russia nickankudinov@gmail.com dsp@ineos.ac.ru.
Abstract:
Organic compounds with boron-nitrogen bonds are widely used as fluorescent sensors and semiconducting materials. This paper presents a new approach for the formation of B-N bonds via catalytic insertion of nitrenes into B-H bonds. The reaction proceeds most selectively for cyclic boranes with a 2-phenylpyridine framework and nitrenes generated in situ by the oxidation of sulfonamides and sulfamates. The most effective catalysts for this process are the readily available rhodium and ruthenium carboxylates of [M2(OOCR)4]X type. Complexes with carboxylate ligands NTTL derived from S-tert-leucine provide unique chiral products with stereogenic boron atoms. The developed method can be used for the introduction of boron heterocycles into biologically active molecules.
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