Development of a practical non-noble metal catalyst for hydrogenation of N-heteroarenes

Veronica Papa, Yixuan Cao, Anke Spannenberg, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

119 Scopus citations

Abstract

Due to their availability, price and biological relevance, the use of catalysts based on 3d transition metals is of substantial importance for the synthesis of industrial chemicals, but also for organic synthesis in general. Hence in recent years, especially in homogeneous catalysis, the use of such Earth-abundant, biocompatible metals has become a major area of interest. However, to achieve reactivity comparable to that of noble-metal catalysts, generally sophisticated ligands—typically expensive phosphorus derivatives—have to be used. Here, we report the chemoselective reduction of quinolines and related N-heterocycles by molecular hydrogen, using a simple Mn(i) complex [Mn(CO)5Br]. Under very mild reaction conditions this catalytic system is able to reduce a wide range of quinolines, affording high yields of the corresponding tetrahydroquinolines, a scaffold present in many bioactive compounds, including marketed pharmaceuticals. Mechanistic studies reveal the formation of the active catalyst and also show the important role of a concomitantly formed Mn(ii) species and HBr for the hydrogenation of the heterocyclic substrates.

Original languageEnglish
Pages (from-to)135-142
Number of pages8
JournalNature Catalysis
Volume3
Issue number2
DOIs
StatePublished - 1 Feb 2020
Externally publishedYes

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