C–H Allylation and [3 + 2] Dipolar Cycloaddition between Azomethine Imines and Vinyl Cyclopropanes under Rh(III) Catalysis

Chaeeun Kim; Anand Kumar; Ju Young Kang; Taejoo Jeong; Hyejin Kim; Soo Bong Han; Pargat Singh; Amitava Rakshit; In Su Kim

doi:10.1021/acs.orglett.6c01877

June 2, 2026Organic Letters

C–H Allylation and [3 + 2] Dipolar Cycloaddition between Azomethine Imines and Vinyl Cyclopropanes under Rh(III) Catalysis

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Key Points

This research investigates the C–H functionalization of azomethine imines using rhodium(III) catalysis to form complex products.
Utilized rhodium(III) as a catalyst for C–H allylation with vinyl cyclopropanes.
Examined the mechanism involving olefin insertion and β-C elimination.
Conducted post-transformations to show the versatility in synthesizing malonate-containing N-heterocycles.
Successfully formed indenopyrazolopyrazolones via [3 + 2] dipolar cycloaddition with a high yield.
Demonstrated the synthetic potential of this method in generating complex tetracyclic structures.
Observed efficient allylation of azomethine imines, supporting the proposed mechanism.

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Implication

Evaluates C–H functionalization effectiveness in azomethine imines, suggesting synthetic advancements.

Abstract

A rhodium(III)-catalyzed C–H functionalization of azomethine imines with vinyl cyclopropanes (VCPs) is proposed. Mechanistically, VCPs participate in olefin insertion and β-C elimination to produce allylated intermediates, which undergo endotype [3 + 2] dipolar cycloaddition, providing indenopyrazolopyrazolones. Post-transformations of malonate-containing tetracyclic N-heterocycles highlight the synthetic relevance of the proposed method.

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Kim et al. (2026) studied this question.

synapsesocial.com/papers/6a2266f6763171746d545d37 https://doi.org/10.1021/acs.orglett.6c01877

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C–H Allylation and [3 + 2] Dipolar Cycloaddition between Azomethine Imines and Vinyl Cyclopropanes under Rh(III) Catalysis

Key Points

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Implication

Abstract

Discussion

Cite This Study

C–H Allylation and [3 + 2] Dipolar Cycloaddition between Azomethine Imines and Vinyl Cyclopropanes under Rh(III) Catalysis

Key Points

Ask about this paper

Implication

Abstract

Discussion

Cite This Study

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