Copper‐Catalyzed C–H Insertion of N ‐Heterocycles Into Diazo Arylidene Succinimides

Copper(II) triflate is found to be an effective catalyst for the regioselective C–H insertion of heteroaromatic compounds into diazo arylidene succinimide‐based carbene precursors. Preferential C3–H insertion occurs in N ‐substituted and unsubstituted indoles, while selective C2–H insertion occurs when the C3 site is blocked. This technique was extended to other heteroaromatic compounds, such as carbazoles, phenothiazines and pyrrole, and all of them yielded the respective C–H insertion products in good yields.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-10-15
DOI
https://doi.org/10.1002/ejoc.70890
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00

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article

Copper‐Catalyzed C–H Insertion of N ‐Heterocycles Into Diazo Arylidene Succinimides

Kannupal Srinivasan, Arputharaj Francisgracia
European Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
article

Copper‐Catalyzed C–H Insertion of N ‐Heterocycles Into Diazo Arylidene Succinimides

Kannupal Srinivasan, Arputharaj Francisgracia
article en

Abstract

Copper(II) triflate is found to be an effective catalyst for the regioselective C–H insertion of heteroaromatic compounds into diazo arylidene succinimide‐based carbene precursors. Preferential C3–H insertion occurs in N ‐substituted and unsubstituted indoles, while selective C2–H insertion occurs when the C3 site is blocked. This technique was extended to other heteroaromatic compounds, such as carbazoles, phenothiazines and pyrrole, and all of them yielded the respective C–H insertion products in good yields.

European Journal of Organic Chemistry
Bharathidasan University (IN)
Department of Science and Technology, Ministry of Science and Technology, India
Openalex Percentile: Top 26%
Cyclopropane Reaction Mechanisms
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