gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides DOI Creative Commons
Monika Bilska‐Markowska, Marcin Kaźmierczak, Wojciech Jankowski

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2946 - 2953

Published: Nov. 15, 2024

The incorporation of fluorine atoms within the structure organic compounds is known to exert a significant impact on their electronic properties, thereby modulating reactivity in diverse chemical transformations. In context our investigation, we observed striking illustration this phenomenon. A Michael addition involving gem -difluorovinyl and trifluorovinyl acceptors was successfully achieved, demonstrating high stereoselectivity. This selectivity further elucidated through theoretical calculations. Using methodology, series new α,β-unsaturated amides, both fluorinated nonfluorinated, were synthesized.

Language: Английский

Photoredox-Catalyzed Sequential Decarboxylative/Defluorinative Aminoalkylation of CF3-Alkenes with N-Arylglycines DOI
Xin Hong, Lu Zhang, Jian Liao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(28), P. 6030 - 6034

Published: July 8, 2024

A photoredox-catalyzed sequential decarboxylative/defluorinative aminoalkylation of CF3-alkenes with N-arylglycines is described. This metal-free and redox-neutral protocol provided efficient access to the monofluoroalkenyl-1,5-diamines in good yields excellent functional group compatibility. Mechanistic studies revealed that reaction proceeds via a radical pathway gem-difluoroalkenyl amine as an intermediate.

Language: Английский

Citations

5
Construction of Benzoxazole and Isoquinoline Compounds via Base-Mediated Cyclization of Amino Acid Derivatives DOI

Yilian Song,

Zechao Liu,

Chuangchuang Liu

et al.

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

Published: March 19, 2025

Biological organisms contain bioactive macromolecules such as amino acids, which serve basic materials for constructing cells and repairing tissues. Due to the unique properties of fluorine atom, can alter structure proteins increase their lipophilicity, incorporating a atom into acids has become research hotspot. In this study, ethyl 3-bromo-2-((diphenylmethylene)amino)-3,3-difluoropropanoate was synthesized from glycine derivatives. Under alkaline conditions, compound reacted with 2-aminophenol generate benzoxazole-containing acid derivative. This method is simple operate, without metal participation, performed under relatively eco-friendly reaction providing novel approach synthesis benzoxazole heterocycles.

Language: Английский

Citations

0
Palladium-Catalyzed Hiyama Cross-Coupling of Heterocyclic Phosphonium Salts with Arylsilanes DOI
Yaqi Liu, Rui Yang, Hongfang Li

et al.

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

Published: April 14, 2025

We report herein the palladium-catalyzed Hiyama cross-coupling of heterocyclic phosphonium salts with diverse (hetero)arylsilanes through C-P bond cleavage, providing an alternative approach for highly regioselective functionalization pyridines and relevant nitrogen-containing heterocycles. This silicon-based protocol is amenable to gram-scale synthesis also applicable late-stage pharmaceutically complex molecules.

Language: Английский

Citations

0
Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes DOI

Zimin Wang,

Daniel C. Hong,

Hongfang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-difluorocyclopropanes with structurally diverse (hetero)arylsilanes through C-C bond activation and C-F cleavage. This regioselective features a broad substrate scope excellent functional group compatibility, affording variety linear 2-fluoroallylic scaffolds in good yields high Z-selectivity.

Language: Английский

Citations

0
Horizons in catalyst-transfer polymerization research DOI Creative Commons
Jônatas Faleiro Berbigier, Bryton R. Varju,

Jiang Tian Liu

et al.

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 538, P. 216724 - 216724

Published: April 21, 2025

Language: Английский

Citations

0
Borane-Catalyzed Coupling of Diazooxindoles and Difluoroenoxysilanes to Tetrasubstituted Monofluoroalkenes DOI

Chunhu He,

Guoyi Zhou,

Guichun Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5539 - 5543

Published: June 24, 2024

A highly stereoselective coupling reaction of diazooxindoles with difluoroenoxysilanes catalyzed by Lewis acidic boranes has been developed. The proceeded at ambient temperature under transition metal-free conditions wide functional group tolerance. By using this simple procedure, a series tetrasubstituted monofluoroalkenes can be accessed in good yield high selectivity.

Language: Английский

Citations

1
Palladium and Copper Co-Catalyzed Chloro-Arylation of gem-Difluorostyrenes – Use of a Nitrite Additive to Suppress β-F Elimination DOI Creative Commons
Andrew J. Intelli,

Coriantumr Z. Wayment,

R. T. LEE

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The installation of fluorine and fluorinated functional groups in organic molecules perturbs the physicochemical properties those enables development new therapeutics, agrichemicals, biological probes materials. However, current synthetic methodologies cannot access some scaffolds. One such group,

Language: Английский

Citations

1
Hiyama Cross-Coupling of gem-Difluoroalkenes: Stereoselective Synthesis of Tetrasubstituted Olefins DOI
Mark Lautens, Jonathan Bajohr

Synfacts, Journal Year: 2024, Volume and Issue: 20(03), P. 0269 - 0269

Published: Feb. 14, 2024

Key words palladium catalysis - Hiyama cross-coupling tetrasubstituted olefins

Language: Английский

Citations

0
gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides DOI Creative Commons
Monika Bilska‐Markowska, Marcin Kaźmierczak, Wojciech Jankowski

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2946 - 2953

Published: Nov. 15, 2024

The incorporation of fluorine atoms within the structure organic compounds is known to exert a significant impact on their electronic properties, thereby modulating reactivity in diverse chemical transformations. In context our investigation, we observed striking illustration this phenomenon. A Michael addition involving gem -difluorovinyl and trifluorovinyl acceptors was successfully achieved, demonstrating high stereoselectivity. This selectivity further elucidated through theoretical calculations. Using methodology, series new α,β-unsaturated amides, both fluorinated nonfluorinated, were synthesized.

Language: Английский

Citations

0