Visible Light Photocatalysis in Water DOI
Camilla Russo, Francesca Brunelli, Gian Cesare Tron

et al.

Published: Nov. 8, 2024

The present chapter aims at introducing the main approaches to developing photocatalytic synthetic methods by using water as a reaction medium. By merging innate green properties of with exploitation renewable energy source, such light, this field research represents one most intensive ones. A selection literature available so far is divided into three sections based on (i) solubility photocatalyst and use additives including surfactants (photomicellar catalysis); (ii) on-water conditions achieve acceleration rates; (iii) photobiocatalytic methods. latter, indeed, are intrinsically designed optimized be performed in an aqueous environment. Taken together, all reactions herein highlighted offer unique opportunities address challenge sustainable manufacturing chemicals.

Language: Английский

Radical Reactions in Organic Synthesis: Exploring in-, on-, and with-Water Methods DOI Creative Commons
Chryssostomos Chatgilialoglu, Sebastián Barata‐Vallejo, Thanasis Gimisis

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(3), P. 569 - 569

Published: Jan. 23, 2024

Radical reactions in water or aqueous media are important for organic synthesis, realizing high-yielding processes under non-toxic and environmentally friendly conditions. This overview includes (i) a general introduction to chemistry media, (ii) synthetic approaches in, on, with as well heterogeneous phases, (iii) of carbon-centered radicals (or deuterium oxide) activated through coordination various Lewis acids, (iv) photocatalysis (v) applications bioinspired by naturally occurring processes. A wide range chemical strategies different experimental conditions have been reviewed that lead functional group translocation transformation reactions, leading the preparation complex molecules. These results reveal how solvent/medium/reagent radical has matured over last two decades, further discoveries anticipated near future.

Language: Английский

Citations

8

Acylmonofluoromethylation of alkenes via dual NHC/photoredox catalysis DOI
Shichao Tian, Mingxi Chen, Yihan Tang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6124 - 6130

Published: Jan. 1, 2023

We herein describe a three-component radical acylmonofluoromethylation of alkenes by cooperative NHC/photoredox catalysis to synthesize various monofluorinated alkyl aryl ketones.

Language: Английский

Citations

11

Dicarbofunctionalization of unactivated alkenes via organo-photoredox catalysis in water: access to cyanoalkylated fused quinazolinones DOI

Abuthayir Mohamathu Ghouse,

Srirama Murthy Akondi

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(26), P. 5351 - 5355

Published: Jan. 1, 2023

An organophotocatalyzed synthesis of polycyclic quinazolinones with a distal nitrile group is reported in the aqueous medium.

Language: Английский

Citations

9

Photoredox-catalyzed direct C–H monofluoromethylation of heteroarenes DOI
Nagarajan Ramkumar,

Ketrina Plantus,

Melita Ozola

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(44), P. 20642 - 20652

Published: Jan. 1, 2023

We report a photo-redox catalyzed radical C–H monofluoromethylation of heterocycles, thus demonstrating this process and the importance monofluoromethyl unit in medicinal drug discovery purposes.

Language: Английский

Citations

5

Iodine-Promoted Disproportionate Coupling Reaction of Arylsulfonyl Hydrazides: A Simple and Green Access to Thiosulfonates DOI
Qi Chen,

Zhao-Hua Chen,

Shi‐Wei Yu

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(09), P. 1415 - 1421

Published: Jan. 17, 2024

Abstract An environmentally friendly iodine-promoted disproportionate coupling reaction of arylsulfonyl hydrazides is reported. This strategy can synthesize thiosulfonates with medium to excellent yields, and features a green system, wide applicability substrates, easy availability raw materials. The preliminary mechanistic study reveals that iodine plays an important role in the radical process.

Language: Английский

Citations

1

Direct Synthesis of Monofluoromethylthioesters from Acyl Chlorides with Elemental Sulfur and Fluoroiodomethane DOI
Chenchen Hu,

Yuyang Zhang,

Zeguo Fang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(24)

Published: April 24, 2024

Abstract We report an unprecedented Ni‐catalyzed direct monofluoromethylthiolation of acyl chlorides, in situ generated from carboxylic acids, with elemental sulfur (S 8 ) as the S source and fluoroiodomethane (ICH 2 F) CH F radical to produce a series monofluoromethylthioesters moderate good yields. This approach features excellent functional group tolerance broad substrate scope. Additionally, late‐stage complex bioactive molecules can also be accomplished using this method.

Language: Английский

Citations

1

1,3-Hydro-di/monofluoromethylation of N,N’-Cyclic Azomethine Imines with HCF2SO2Na/H2CFSO2Na via Photocatalytic Radical Addition DOI

Min Kou,

Jianli Zheng,

Feifei Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11747 - 11752

Published: July 31, 2024

The radical 1,3-hydro-di/monofluoromethylation of N,N'-cyclic azomethine imines with HCF2SO2Na/H2CFSO2Na via photoredox catalysis is described. This reaction exhibits broad functional group compatibility, providing the desired products in good yields. However, CF3SO2Na failed to produce trifluoromethyl product. DFT calculations revealed that transition state activation energy for trifluoromethylation was significantly higher and isotropic charge repulsion makes it difficult CF3 transfer electrons.

Language: Английский

Citations

1

Photoredox-Catalysis Fluorosulfonyldifluoromethylation of Unactivated Alkenes and (Hetero)arenes with ICF2SO2F DOI

Xu-Biao He,

Xin Jia,

Pinqiao Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6900 - 6904

Published: Aug. 8, 2024

The fluorosulfonyldifluoromethylation of unactivated alkenes and (hetero)arenes with iododifluoromethanesulfonyl fluoride (ICF

Language: Английский

Citations

1

Visible-Light-Induced Difunctionalization of 3-Butenoic Acid with Bromodifluoromethyl Heteroarylsulfones DOI
Qianqian Liu, Xiaoping Wang,

Xuefeng Gu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6449 - 6453

Published: July 22, 2024

Herein, we report a visible-light-induced iridium-promoted direct bifunctionalization of 3-butenoic acid with bromodifluoromethyl heteroarylsulfones. This methodology enables the concurrent introduction difluoromethyl heteroarylsulfone and bromine groups into under mild reaction conditions. Various

Language: Английский

Citations

0

Chemoselective Hydroheteroarylation of Alkenes via Photoredox-Neutral Proton- and BF3-Mediated Electron Transfer DOI

Xiaoyuan Wan,

Huawen Huang,

Deng Yujie

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7707 - 7712

Published: Aug. 28, 2024

Herein, we have developed a complementary entry to enable hydroheteroarylation of alkenes involving basically photoredox dearomatizative heterocyclic carbon radical formation through acid-coupled electron transfer followed by Giese addition. While protonic solvent and thiophenol additive enabled two molecular hydroheteroarylations alkenes, the nonproton environment with BF

Language: Английский

Citations

0