ArticleJACS Au2024
Selective [3 + 2] C-H/C-H Alkyne Annulation via Dual (Distal) C
Article in JACS Au, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
1 citing paper in PubMed.
- Pd(II)-Catalyzed C-H Activation/ACS omega · 2026Article
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Authors and funding
12 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In contrast to proximal C-H bond activations, distal C-H bond activation is fundamentally more challenging and requires distinctly specialized directing partners or techniques. In this context, we report an unprecedented dual (distal) β-C(benzylic)-H and δ-C(aryl)-H bond activation relay protocol for the chemo-, regio-, and stereoselective construction of heterocycle-tethered benzofulvenes via [3 + 2] CH/CH-alkyne annulation under palladium catalysis. The protocol overrides the more favorable [4 + 2] CH/NH annulation and does not follow the vinylic C-H bond activation pathway. Mechanistic studies provide insight into the favored cyclopalladation of key intermediates (resulting from β-C(benzylic)-H bond cleavage) through relay δ-C(aryl)-H cleavage (vs N-H cleavage) prior to reductive elimination, which is the key to desired annulation. The synthesized new chemical entities (NCEs) constitute a novel scaffold with favorable anticancer activity against oral squamous cell carcinoma (OSCC). Detailed biomolecular studies, including RNA-sequencing and analysis, indicate that these compounds (
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