Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines DOI
Xiaolong Wang, Yan Fu,

Zhenshan Guo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence any catalyst or additive, C5-selective could proceed at room temperature. With palladium used as catalyst, selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, scale-up application. The potential utilities products were shown by further transformations.

Language: Английский

Thermocontrolled Radical Nucleophilicity vs Radicophilicity in Regiodivergent C–H Functionalization DOI

Buddhadeb Pal,

Prasenjit Mal

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 8, 2025

The temperature-dependent switching behavior of the saccharin radical is demonstrated, enabling regiodivergent C3–H and C7–H functionalization quinoxalin-2(1H)-ones. was generated through N–Br bond cleavage in N-bromosaccharin (NBSA) observed to transition between radicophile roles. At −10 °C, it utilized as a radicophile, resulting 100% C3-amination, while at +35 acted radical, leading exclusive C7-bromination. Radical nucleophilicity controlled by temperature modulation.

Language: Английский

Citations

0
Boron Compounds as Key Drivers of Innovation: Exploring Their Role in Environmental Remediation, Sustainable Agriculture, Advanced Biomedical Applications, and Green Chemistry DOI
Metin Yıldırım, Mehmet Erşatır, Mohammed Saleh

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123688 - 123688

Published: April 1, 2025

Language: Английский

Citations

0
Catalytic photoinduced deoxygenation via B(C6F5)3-enabled OAT for aromatic C−H amination of alkylarenes DOI
Yongmin Ma

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Abstract The catalytic deoxygenation of N − OH bonds to generate N-centered radicals remains a significant challenge due the high bond dissociation energy and reliance on stoichiometric auxiliaries or activators. Herein, we report B(C6F5)3-catalyzed photoinduced strategy that enables direct aromatic C(sp²) H amination alkylarenes using N-hydroxyphthalimides (NHPIs) as nitrogen sources. Mechanistic studies reveal in situ formation PhthN O−B(C6F5)3 anion intermediate facilitates an unusual transfer (EnT)-mediated O homolysis, generating phthalimidyl radical (PhthN•) while regenerating borane catalyst. This method overrides conventional preference for benzylic C oxidation, achieving exclusive with broad substrate scope, including electron-rich/poor alkylarenes, heteroarenes, biomolecules. protocol operates under mild conditions, avoids organic auxiliaries/activators, produces H₂O sole byproduct, thus, making it promising option supplant existing strategies arene amination. Applications in late-stage functionalization pharmaceuticals synthesis nilotinib precursor highlight its synthetic utility. study establishes B(C6F5)3 versatile oxygen atom (OAT) reagent photochemistry, opening avenues sustainable generation.

Language: Английский

Citations

0
Fe (III)-Catalyzed p-Selective C–H Bond Chalcogenation of Phenols DOI
Biprajit Paul, Sayak Ghosh, Surajit Das

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

An efficient, eco-friendly, and scalable protocol has been introduced for the

Language: Английский

Citations

1
π‐Conjugation as a Direct Estimate of Lewis Acidity DOI Creative Commons
Daniel González‐Pinardo, Israel Fernández

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 6, 2024

A computational approach to directly estimate the relative acidity of a given Lewis acid is presented. This based on strength π-conjugation in trans-crotonaldehyde-Lewis complexes, species used well-known Childs' scale. It found that π-conjugative values by Energy Decomposition Analysis - Natural Orbital for Chemical Valence method strongly correlate not only with variation bond lengths system, which are greatly affected nature acid, but also downfield shifts experienced different nuclei conjugated system upon binding acid. These strong correlations indicate (easy-to-compute) energies can be as an alternative

Language: Английский

Citations

0
Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF3-Substituted Indolines DOI
Xiaolong Wang, Yan Fu,

Zhenshan Guo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence any catalyst or additive, C5-selective could proceed at room temperature. With palladium used as catalyst, selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, scale-up application. The potential utilities products were shown by further transformations.

Language: Английский

Citations

0