Cyclometalated Ruthenium Catalyst Enables Selective Oxidation of N‑Substituted Tetrahydroquinolines to Lactams

Herein, we report an unusual α-methylene oxidation of N-substituted tetrahydroquinoline to lactams using the cyclometalated Ru­(II)-complex as a catalyst. Cyclic-α-methylene C–H bonds are selectively oxidized under the reaction conditions even in the presence of α-methyl or reactive α-methylene C–H...

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Bibliographic Details
Published in:Organic letters 2024-02, Vol.26 (6), p.1184-1189
Main Authors: Konwar, Monuranjan, Das, Tapashi, Das, Animesh
Format: Article
Language:English
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Summary:Herein, we report an unusual α-methylene oxidation of N-substituted tetrahydroquinoline to lactams using the cyclometalated Ru­(II)-complex as a catalyst. Cyclic-α-methylene C–H bonds are selectively oxidized under the reaction conditions even in the presence of α-methyl or reactive α-methylene C–H bonds. This methodology is also useful in the late-stage functionalization of pharmaceuticals. Mechanistic study demonstrates that the high-valent Ru­(VI)-cis-dioxo species plays an important role in controlling selectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c04263