Palladium(II)‐Catalyzed Distal CH Functionalization of 8‐Aminoquinolinamides: Facile Synthesis of Triarylmethane Derivatives

Herein, a straightforward approach is reported for the palladium‐catalyzed oxidative remote CH alkylation of 8‐aminoquinoline derivatives using para‐ quinone methides. This method enables selective C5‐alkylation of quinolines and exhibits a site‐selectivity distinct from that typically observed in convetional palladium‐catalyzed sp 2 CH activation. The reaction proceeds via chelation‐induced remote CH functionalization, and a broad range of quinolinamides are successfully coupled with p ‐quinone methides, demonstrating excellent substrate scope and functional group tolerance. Preliminary mechanistic studies suggest a reversible CH metalation step as part of the catalytic cycle.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-10-08
DOI
https://doi.org/10.1002/ejoc.202500493
Primary Topic
Synthesis of Indole Derivatives
Type
article
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article

Palladium(II)‐Catalyzed Distal CH Functionalization of 8‐Aminoquinolinamides: Facile Synthesis of Triarylmethane Derivatives

Anushka Rastogi, Manoj Kumar Gangwar, Dipankar Koley, M. Ravi Kumar
European Journal of Organic Chemistry
Synthesis of Indole Derivatives
article

Palladium(II)‐Catalyzed Distal CH Functionalization of 8‐Aminoquinolinamides: Facile Synthesis of Triarylmethane Derivatives

Anushka Rastogi, Manoj Kumar Gangwar, Dipankar Koley, M. Ravi Kumar
article en

Abstract

Herein, a straightforward approach is reported for the palladium‐catalyzed oxidative remote CH alkylation of 8‐aminoquinoline derivatives using para‐ quinone methides. This method enables selective C5‐alkylation of quinolines and exhibits a site‐selectivity distinct from that typically observed in convetional palladium‐catalyzed sp 2 CH activation. The reaction proceeds via chelation‐induced remote CH functionalization, and a broad range of quinolinamides are successfully coupled with p ‐quinone methides, demonstrating excellent substrate scope and functional group tolerance. Preliminary mechanistic studies suggest a reversible CH metalation step as part of the catalytic cycle.

European Journal of Organic ChemistryVol. 28(45)
University of Allahabad (IN), Central Drug Research Institute (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 78%
Synthesis of Indole Derivatives
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