Site Selective Heck Arylation of N-Vinyl-7-Azaindole Engineered by N-Oxide Activation: Scope and Mechanistic Studies

Susanta Patra; Arunava Sengupta; Parthasarathi Das

doi:10.1039/d5qo00976f

January 1, 2025Organic Chemistry Frontiers

Site Selective Heck Arylation of N-Vinyl-7-Azaindole Engineered by N-Oxide Activation: Scope and Mechanistic Studies

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Key Points

Complete switch to exclusive β-arylation is achieved through N-oxide activation, enhancing regioselectivity.
The reaction displays moderate regioselectivity favoring α-arylation prior to activation by N-oxide.
Investigation includes scope and mechanistic studies to understand the arylation process in depth.
Results may inform future applications in organic synthesis and medicinal chemistry with enhanced selectivity.

Implication

Palladium-catalyzed arylation shows exclusive β-arylation with N-oxide activation, suggesting novel mechanisms.

Abstract

The palladium-catalyzed site-selective arylation of N-vinyl-7-azaindole (AI) derivatives using (hetero)iodoarenes is reported. While N-vinyl-7-azaindole displays moderate regioselectivity, predominantly favoring α-arylation, N-oxide activation (AINO) induces a complete switch to exclusive β-arylation...

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Cite This Study

Patra et al. (2025) studied this question.

synapsesocial.com/papers/68c18f409b7b07f3a0615df7 https://doi.org/10.1039/d5qo00976f

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Site Selective Heck Arylation of N-Vinyl-7-Azaindole Engineered by N-Oxide Activation: Scope and Mechanistic Studies

Key Points

Implication

Abstract

Discussion

Cite This Study

Site Selective Heck Arylation of N-Vinyl-7-Azaindole Engineered by N-Oxide Activation: Scope and Mechanistic Studies

Key Points

Implication

Abstract

Discussion

Cite This Study

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