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Manganese-Catalyzed and Base-Switchable Synthesis of Amines or Imines via Borrowing Hydrogen or Dehydrogenative Condensation

Title data

Fertig, Robin ; Irrgang, Torsten ; Freitag, Frederik ; Zander, Judith ; Kempe, Rhett:
Manganese-Catalyzed and Base-Switchable Synthesis of Amines or Imines via Borrowing Hydrogen or Dehydrogenative Condensation.
In: ACS Catalysis. Vol. 8 (August 2018) . - pp. 8525-8530.
ISSN 2155-5435
DOI: https://doi.org/10.1021/acscatal.8b02530

Abstract in another language

The use of earth-abundant transition metals as a noble metal replacement in catalysis is especially interesting if different catalytic reactivity is observed. We report, here, on the selective manganese-catalyzed base-switchable synthesis of N-alkylated amines or imines. In both reactions, borrowing hydrogen/hydrogen autotransfer (N-alkyl amine formation) or dehydrogenative condensation (imine formation), we start from the same amines and alcohols and use the same Mn precatalyst. The key is the presence of a potassium base to prefer N-alkylation and a sodium base to permit imine formation. Both bases react with the manganese hydride via deprotonation. The potassium manganate hydride reacts about 40 times faster with an imine to give the corresponding amine than the sodium manganate hydride. The selectivity seems unique for manganese complexes. We observe a broad scope with a complete product overlap, all amine alcohol combinations can be converted into an N-alkyl amine or an imine, and a good functional group tolerance.

Further data

Item Type: Article in a journal
Refereed: Yes
Keywords: amines; base-switchable; borrowing hydrogen; dehydrogenative condensation; imines; manganese; N-alkylation
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Anorganic Chemistry II
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Anorganic Chemistry II > Chair Anorganic Chemistry II - Univ.-Prof. Dr. Rhett Kempe
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Result of work at the UBT: Yes
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 29 Aug 2018 06:59
Last Modified: 29 Aug 2018 06:59
URI: https://eref.uni-bayreuth.de/id/eprint/45608