Photoinduced Remote C(sp3)−H Phosphonylation of Amides DOI
Jian Wang, Yuchen Zhang, Lin Zhu

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(23)

Published: April 4, 2024

Abstract The present study reports an unprecedented protocol for the phosphonylation of unactivated C(sp 3 )−H bonds. By utilizing 1 mol % 4DPAIPN (1,2,3,5‐tetrakis(diphenylamino)‐4,6‐dicyanobenzene) as catalyst, satisfactory yields γ‐phosphonylated amides are obtained through a visible‐light‐induced reaction between N ‐((4‐cyanobenzoyl)oxy)alkanamides and 9‐fluorenyl o ‐phenylene phosphite at room temperature. This demonstrates broad substrate scope wide functional group compatibility.

Language: Английский

Photochemical and Electrochemical Strategies towards Benzylic C−H Functionalization: A Recent Update DOI
Monica Oliva, Guglielmo Coppola, Erik V. Van der Eycken

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(7), P. 1810 - 1834

Published: Feb. 16, 2021

Abstract Transition metal‐catalysed processes have been widely used for the functionalization of inert C−H bonds. Strategies benzylic position having a relatively weak bond (bond dissociation energy∼ 80–90 kcal/mol) differ from aliphatic and aromatic positions with stronger The recent advances in direct activation through generation C( sp 3 ) radicals demonstrated potential electrochemistry photochemistry as means constructing new chemical This review will cover progress organic radical strategies employing sustainable tools. In addition, mechanistic details typical reactions included which, turn, help researchers to look at this promising area different perspective towards discoveries often hidden opportunities. magnified image

Language: Английский

Citations

111

Heterogeneous electrosynthesis of C–N, C–S and C–P products using CO2 as a building block DOI
Junnan Li,

Hamed Heidarpour,

Guorui Gao

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(7), P. 809 - 824

Published: May 17, 2024

Language: Английский

Citations

30

Recent Advances in Paired Electrosynthesis DOI Creative Commons
Frank Marken, Alexander J. Cresswell, Steven D. Bull

et al.

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(9), P. 2585 - 2600

Published: April 8, 2021

Progress in electroorganic synthesis is linked to innovation of new synthetic reactions with impact on medicinal chemistry and drug discovery the desire minimise waste provide energy-efficient chemical transformations for future industrial processes. Paired electrosynthetic processes that combine use both anode cathode (convergent or divergent) minimal (or without) intentionally added electrolyte need additional reagents are growing interest. In this overview, recent progress developing paired electrolytic surveyed. The discussion focuses electrosynthesis technology proven value preparation small molecules. Reactor types contrasted concept translating light-energy driven photoredox into highlighted as a newly emerging trend.

Language: Английский

Citations

72

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024 DOI
Martha C. Mayorquín‐Torres, Andreas Simoens, Eli Bonneure

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(12), P. 7907 - 7975

Published: May 29, 2024

The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search development synthetic routes for obtaining novel members this family compounds. This updated review covers methodologies established since 2004, focusing on synthesis phosphonates, which phosphonate moiety is directly substituted onto to structure. Emphasizing recent advances, classifies newly developed approaches according ring size providing information biological activities whenever available. Furthermore, summarizes various methods formation C–P bonds, examining sustainable such as Michaelis–Arbuzov reaction, Michaelis–Becker Pudovik Hirao coupling, Kabachnik–Fields reaction. After analyzing applications investigated years, a predominant focus evaluation these compounds anticancer agents evident. emerging underline versatility potential compounds, highlighting need continued research expand interesting family.

Language: Английский

Citations

15

Recent advances in the electrochemical synthesis of organophosphorus compounds DOI Creative Commons
Babak Kaboudin, Milad Behroozi,

Sepideh Sadighi

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 770 - 797

Published: April 16, 2025

In this review, we describe recent advances in electrochemical green methods for the synthesis of various organophosphorus compounds through formation phosphorus–carbon, phosphorus–nitrogen, phosphorus–oxygen, phosphorus–sulfur, and phosphorus–selenium bonds. The impact different electrodes is also discussed matter. Graphite, platinum, RVC, nickel have been used extensively compounds. made method a promising preparing structures. This review an introduction to encourage scientists use electrosynthesis as green, precise, low-cost prepare phosphorous

Language: Английский

Citations

1

Recent advances in electrochemical C—H phosphorylation DOI Creative Commons
Yulia H. Budnikova,

Egor L. Dolengovsky,

Maxim V. Tarasov

et al.

Frontiers in Chemistry, Journal Year: 2022, Volume and Issue: 10

Published: Nov. 3, 2022

The activation of C–H bond, and its direct one-step functionalization, is one the key synthetic methodologies that provides access to a variety practically significant compounds. Particular attention focused on modifications obtained at final stages synthesis complicated molecules, which requires high tolerance presence existing functional groups. Phosphorus an indispensable element life, phosphorus chemistry now experiencing renaissance due new emerging applications in medicinal chemistry, materials (polymers, flame retardants, organic electronics, photonics), agricultural (herbicides, insecticides), catalysis (ligands) other important areas science technology. In this regard, search for new, more selective, low-waste routes become relevant. context, electrosynthesis has proven be eco-efficient convenient approach many respects, where reagents are replaced by electrodes, reactants applied potential determines their “oxidizing or reducing ability”. An electrochemical such processes being developed rapidly demonstrates some advantages over traditional classical methods C-H phosphorylation. main reasons success exclusion excess from reaction system: as oxidants, agents, sometimes metal and/or improvers, challenge isolation, increase wastes reduce yield frequent incompatibility with these Ideal conditions include electron reactant (regulated potential) by-products hydrogen hydrocarbon. review summarizes analyzes achievements preparation various derivatives carbon-phosphorus bonds, collects data redox properties most commonly used precursors. Electrochemically induced reactions both without catalyst metals, competitive oxidation precursors leads either bond generation phosphorus-centered radicals (radical cations) states will examined. focuses publications past 5 years.

Language: Английский

Citations

29

Metal-free direct C–H phosphonation of N-heterocycles with diphenylphosphine oxides under mild conditions DOI

Zhaonan Cai,

Yaping Han, Yuecheng Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(14), P. 5721 - 5726

Published: Jan. 1, 2023

Herein, metal-free phosphonation of N-heterocycles with diphenylphosphine oxides, promoted by 1,5-diazabicyclo[5,4,0]undec-5-ene utilizing air as a green oxidant in dimethyl carbonate an eco-friendly solvent at room temperature, is presented.

Language: Английский

Citations

17

Electrochemical Phosphorylation of Organic Molecules DOI Creative Commons
Najoua Sbei, Guilherme M. Martins, Bahareh Shirinfar

et al.

The Chemical Record, Journal Year: 2020, Volume and Issue: 20(12), P. 1530 - 1552

Published: Oct. 5, 2020

Abstract Organophosphorus chemistry is a broad field with multi‐dimensional applications in research area of organic, biology, drug design and agrochemicals. Conventional methods have been adopted extensively to access phosphorylated compounds that rely on the use toxic, moisture sensitive phosphorylating agents occur presence oxidants, catalysts, as well high temperatures harsh conditions are required for complete transformations. However, recent progress has made phosphorylation reactions using electricity introduce green sustainable synthetic procedures. These can be performed at mild proceed excellent atom economy. Herein, we targeted electrochemical generation new bonds such C(sp 3 ) −P, 2 O−P, N−P, S−P Se−P. This review aimed offer an overview developments methodology easy organophosphorus electrochemistry.

Language: Английский

Citations

47

Recent advances in paired electrolysis and their application in organic electrosynthesis DOI
Gerhard Hilt

Current Opinion in Electrochemistry, Journal Year: 2023, Volume and Issue: 43, P. 101425 - 101425

Published: Nov. 20, 2023

Language: Английский

Citations

16

Photoinduced Remote C(sp3)−H Phosphonylation of Amides DOI
Jian Wang, Yuchen Zhang, Lin Zhu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(23)

Published: April 4, 2024

The present study reports an unprecedented protocol for the phosphonylation of unactivated C(sp

Language: Английский

Citations

6