Cobalt-Catalyzed C–H Activation/Annulation of <i>N</i> -(Naphthalen-1-yl)amides with Isocyanides: Synthesis of Benzo[ <i>c,d</i> ]indol-2-imines

This study unveils the first cobalt-catalyzed picolinamide-directed C-H/N-H annulation of <i>N</i>-(naphthalen-1-yl)picolinamide with isocyanides, which efficiently forms benzo[<i>c,d</i>]indol-2-imines via peri-C-H activation. Using Ag<sub>2</sub>O and mild conditions, it offers a cost-effective, atom-economical route with a broad substrate scope and in situ directing group removal for simplified synthesis and good yields.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-09
DOI
https://doi.org/10.1021/acs.joc.5c02937
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Cobalt-Catalyzed C–H Activation/Annulation of N -(Naphthalen-1-yl)amides with Isocyanides: Synthesis of Benzo[ c,d ]indol-2-imines

Mahesh Sonawane, Raj N. Patel, S. P. Ghosh
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Cobalt-Catalyzed C–H Activation/Annulation of N -(Naphthalen-1-yl)amides with Isocyanides: Synthesis of Benzo[ c,d ]indol-2-imines

Mahesh Sonawane, Raj N. Patel, S. P. Ghosh
article en

Abstract

This study unveils the first cobalt-catalyzed picolinamide-directed C-H/N-H annulation of <i>N</i>-(naphthalen-1-yl)picolinamide with isocyanides, which efficiently forms benzo[<i>c,d</i>]indol-2-imines via peri-C-H activation. Using Ag<sub>2</sub>O and mild conditions, it offers a cost-effective, atom-economical route with a broad substrate scope and in situ directing group removal for simplified synthesis and good yields.

The Journal of Organic ChemistryVol. 91(3)
Central Salt and Marine Chemicals Research Institute (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 94%
Catalytic C–H Functionalization Methods
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