Access to Fluorinated Dienes through Hydrofluorination of 2-En-4-ynoates DOI Creative Commons
Yue Xia,

Aaron D. Charlack,

Ruibin Guo

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

The hydrofluorination of enynoates has been developed for the synthesis fluorinated dienoates.

Language: Английский

Ambiphilic Reactivity of SF5‐Alkynes Applied to Regioselective and Stereodivergent Halogenation Reactions: An Experimental and Theoretical Case Study DOI Creative Commons
David Matchavariani, Lucas Popek, Jorge Juan Cabrera‐Trujillo

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(16), P. 3481 - 3493

Published: April 25, 2024

Abstract We explored the ambiphilic reactivity of SF 5 ‐alkynes, and we proved they can act as both nucleophiles electrophiles. selected halogenation reactions benchmark developed highly selective stereodivergent hydrohalogenation (I, Br, Cl, F) ‐alkynes. The stereochemistry is finely controlled thanks to nature acids used (strong or soft) in presence halide source, while high regioselectivity governed by strong polarization Mechanistic studies supported DFT calculations shed light on two different reaction mechanisms responsible excellent stereocontrol. This stereoselectivity was quantitatively rationalized with ASM EDA methods. A few dihalogenation are reported rationalize this cis ‐stereoselectivity. Relative configuration all ‐haloalkenes unambiguously determined X‐ray diffraction. Noteworthy, several post‐functionalization such cross‐couplings, cyanation reductions described strengthen synthetic potential.

Language: Английский

Citations

7

Recent advances in the chemistry and the application of SF5-compounds DOI
Mariam Abd El Sater, Lucas Popek, Nicolas Blanchard

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 9, 2024

Abstract This review article outlines the literature from 2022 to 2024 covering developments in SF5 chemistry. Recent synthetic methodologies of SF5-containing building blocks are reported. These methods include synthesis SF5Cl and its use pentafluorosulfanylation reactions oxidative fluorination reactions. Moreover, reactivity SF5-alkynes as versatile platform access new SF5-compounds is described. Finally, effects moiety highlighted according application different fields, such biological/medicinal chemistry, catalysis, material sciences. 1 Introduction 2 Access SF5-Containing Building Blocks 2.1 By Means 2.1.1 Generation 2.2 Oxidative Fluorination 2.3 SF5-Alkynes 2.4 Other Miscellaneous Aromatic Aliphatic SF5-Compounds 3 Applications 3.1 Medicinal Biological Chemistry 3.2 Material Science 3.3 Catalysis 4 Conclusion

Language: Английский

Citations

7

Radical trifluoromethoxylation of fluorinated alkenes for accessing difluoro(trifluoromethoxy)methyl groups DOI Creative Commons

Koki Kawai,

Mai Usui,

Sota Ikawa

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

In this study, we explore the potential of difluoro(trifluoromethoxy)methyl group, CF 2 –O–CF 3 , an underexplored but promising structural analog trifluoromethoxy group (OCF ).

Language: Английский

Citations

1

Palladium-Catalyzed Regioselective Monofluoroallylation of Indoles with gem-Difluorocyclopropanes DOI
Zhenjie Wang, Chuang Liu, Junhai Huang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6905 - 6909

Published: Aug. 1, 2024

We present a palladium-catalyzed ring-opening reaction that induces indoles to cross-couple with gem-difluorocyclopropanes. The proceeds through domino process of C–C bond activation and C–F elimination, followed by C–C(sp2) coupling produce various 2-fluoroallylindoles. This method is characterized its high functional group tolerance, good yields regioselectivity, under base-free conditions. synthetic utility the products illustrated functionalization NH C2 positions indole scaffold.

Language: Английский

Citations

5

Chemoselective Csp2‐H Radical Alkylation of Aryl Diazonium Salts with 1‐Iodo‐3‐Pentafluorosulfanylbicyclo[1,1,1]pentane (SF5BCP‐I) DOI Open Access
Xin Zhao, Xinyu Li,

Jia‐Yi Shou

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

Comprehensive Summary The reaction site of aryl diazonium salt was restricted in the position moiety, due to intrinsic electrophilicity moiety. Herein, we described an unprecedented chemoselective alkylation Csp 2 ‐H salts with 1‐iodo‐3‐pentafluorosulfanylbicyclo[1,1,1]pentane (SF 5 ‐BCP‐I). This novel provided efficient access various SF ‐BCP substituted aromatics that might have great potential application drug discovery. Mechanistic experiments and theoretical studies revealed electrophilic radical resulted thermodynamic favorable addition on rather than moiety salt.

Language: Английский

Citations

0

Recent achievements in the synthesis and reactivity of pentafluorosulfanyl-alkynes DOI Creative Commons

Floriane René,

Léo Clément–Comoy,

Nicolas Blanchard

et al.

Comptes Rendus Chimie, Journal Year: 2024, Volume and Issue: 27(G1), P. 227 - 240

Published: Nov. 7, 2024

In the dynamic field of pentafluorosulfanyl (SF5) chemistry, SF5-alkynes have emerged as essential, readily accessible, and modular building blocks for construction a wide variety SF5-containing molecules. This polarized platform has been used to perform highly regio-, chemo-, stereoselective transformations such heterocycle synthesis, cycloaddition, hydroelementation reactions. brief review provides an overview recent developments in synthesis reactivity SF5-alkynes, which are fascinating that yet reveal their full synthetic potential. Dans le domaine dynamique de la chimie du groupement pentafluorosulfanyle (SF5), les alcynes SF5 sont apparus comme des éléments base essentiels, facilement accessibles et modulaires pour d'une grande variété molécules contenant SF5. Cette plateforme polarisée été utilisée effectuer hautement régio-, chimio- stéréosélectives telles que synthèse d'hétérocycles, réactions cycloaddition d'hydroélémentation. brève revue présente un aperçu dernières avancées concernant réactivité SF5, briques élémentaires qui n'ont pas encore révélé tout leur potentiel synthèse.

Citations

2

TBHP Promotes Cross-Dehydrogenative Coupling of SF4 Alkynes with Tetrahydroisoquinolines under Copper Catalysis DOI

Srikanth Reddy Narra,

Putri Nur Arina Mohd Ariff,

Debarshi Saha

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7370 - 7375

Published: Aug. 23, 2024

We present a viable approach for the cross-dehydrogenative coupling of Het-SF4-alkynes with tetrahydroisoquinolines under oxidative conditions, using TBHP and copper catalysts. These newly developed conditions boast enhanced yields more extensive range substrates, demonstrating tolerance to various functional groups addressing limitations earlier reports. Consequently, this method should increase opportunities exploration SF4-containing compounds their potential applications in drug discovery, materials science, as alternatives PFAS.

Language: Английский

Citations

0

Access to Fluorinated Dienes through Hydrofluorination of 2-En-4-ynoates DOI Creative Commons
Yue Xia,

Aaron D. Charlack,

Ruibin Guo

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 17, 2024

The hydrofluorination of enynoates has been developed for the synthesis fluorinated dienoates.

Language: Английский

Citations

0