Phosphirane-Enabled Synthesis of Aromatic 1H-1,2-Azaphospholes and Phosphinines DOI

Chenyong Xu,

Zhipeng Dai,

Shaopeng Kang

et al.

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

Published: Dec. 6, 2024

Aromatic heteroarenes are essential components of numerous valuable molecules. Herein we present a simple and effective route to access aromatic 1H-1,2-azaphospholes phosphinines. This method utilizes the ring tension phosphiranes convert β-chloroethylphosphane alkynyl imines into these compounds. The nucleophilic addition phosphiranide complex results in 3, which transform under mild conditions. skeletal editing 1,2-azaphospholes phosphinine derivatives was accomplished through cascade process involving [4 + 2] cycloaddition elimination nitrogen moiety.

Language: Английский

Nitrous oxide as diazo transfer reagent DOI Creative Commons
Alexandre Genoux, Kay Severin

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13605 - 13617

Published: Jan. 1, 2024

The review summarizes the use of nitrous oxide (N 2 O, ‘laughing gas’) as a diazo transfer reagent in synthetic chemistry.

Language: Английский

Citations

6
Trendbericht Anorganische Chemie 2024: Hauptgruppen‐ und Molekülchemie DOI Open Access
Josh Abbenseth, Frank Tambornino

Nachrichten aus der Chemie, Journal Year: 2025, Volume and Issue: 73(2), P. 46 - 55

Published: Jan. 31, 2025

Abstract Das erste heterobimetallische Dimetallocen; mit sterisch anspruchsvollen Liganden lassen sich einfach‐koordinierte Hauptgruppenverbindungen der Gruppen 13 bis 15 herstellen; neue Diazoverbindungen erlauben es, B‐R‐Einheiten und Kohlenstoffatome zu übertragen.

Citations

0
A Tandem Route toward Isoxazolidine Fused Phospholene Skeleton Involving Dearomative [3+2] Cycloaddition of P‐Heteroarenes and Nitrones DOI Open Access

Chenyong Xu,

Y. Wang, Meng Xiao

et al.

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

Published: Feb. 19, 2025

Comprehensive Summary The demands for effective assembly of structurally complex molecular scaffolds from simple starting materials are continuously growing along with the development organic chemistry. We have developed a tandem approach that assembles β ‐chloroethylphosphane, alkynyl imines (or ketones), and nitrones into isoxazolidine fused phospholene through sequential process involving phospha‐Michael addition, intramolecular cyclization, dearomatizing [3+2] cycloaddition reactions. isoxazolidine‐fused has three heteroatoms, including junction phosphorus atom. After removing coordinated tungsten group, these compounds can serve as potential P‐stereogenic ligands may biological activities. Contrary to pyrroles furans, aromatic 2‐phosphapyrroles 2‐phosphafurans good 2π‐electron candidates in dearomative reactions due poor overlap 2p‐3p orbitals C=P moiety.

Language: Английский

Citations

0
Chlorine-free synthesis of axially chiral organophosphorus compounds from white phosphorus DOI
Xinlei Huangfu, Yunguo Liu, Zhiyi Song

et al.

Chem, Journal Year: 2025, Volume and Issue: unknown, P. 102496 - 102496

Published: March 1, 2025

Language: Английский

Citations

0
Combining Distibene, Diazoolefins, and Visible Light: Synthesis and Reactivity of Inorganic Rings DOI
Prasenjit Palui,

Sangita Ghosh,

Rosa M. Gomila

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 7, 2025

The chemistry of heterocycles containing "diaza" units has been extensively studied due to their applications ranging from pharmaceuticals advanced materials. In contrast, incorporating heavier elements, such as Sb and Bi, remain exceedingly rare lack straightforward synthetic methodologies. Herein, we present a comprehensive experimental theoretical investigation the first diazadistiboylidenes (1a, 1b), synthesized via [3 + 2]-cycloaddition between distibene diazoolefins. These stiboylidenes are key intermediates promote selective nucleophilic substitution, leading example diantimonyl anion. Furthermore, upon visible-light irradiation, could isolate methylenedistibiranes, analogs methylenediaziridine (C2H4N2). findings offer novel platform for heavy dipnictogen chemistry, showcasing that diazoolefins, in combination with visible light, can facilitate formation unprecedented serve CO2 activation.

Language: Английский

Citations

0
Phosphirane-Enabled Synthesis of Aromatic 1H-1,2-Azaphospholes and Phosphinines DOI

Chenyong Xu,

Zhipeng Dai,

Shaopeng Kang

et al.

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

Published: Dec. 6, 2024

Aromatic heteroarenes are essential components of numerous valuable molecules. Herein we present a simple and effective route to access aromatic 1H-1,2-azaphospholes phosphinines. This method utilizes the ring tension phosphiranes convert β-chloroethylphosphane alkynyl imines into these compounds. The nucleophilic addition phosphiranide complex results in 3, which transform under mild conditions. skeletal editing 1,2-azaphospholes phosphinine derivatives was accomplished through cascade process involving [4 + 2] cycloaddition elimination nitrogen moiety.

Language: Английский

Citations

2