Photocatalyst-Free Transformation of C(sp3)–H Bonds to Oxime Ethers via Photoinduced Hydrogen Atom Transfer DOI

Yulian Zhao,

Xuehong Min,

Lijing Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9383 - 9388

Published: Oct. 22, 2024

Herein, a direct transformation of aliphatic C–H bonds to oxime ethers has been developed via light-promoted hydrogen atom transfer (HAT) in the absence photocatalyst. Singlet oxygen and chlorine radical are complementary C(sp3)–H bond cleaving agents this reaction, enabling extraction atoms from diverse range compounds, like cycloalkanes, ethers, amines, amides, cyclic sulfides. This method excels transforming common into valuable featuring abundant chemical feedstocks, good functional group tolerance, catalyst free conditions.

Language: Английский

Recent Advances in Deoxygenative Thioether Synthesis Using Oxygenated Sulfur Surrogates DOI
Cong Ma, Long Yin Lam

Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Abstract Thioethers (sulfides) play a crucial role in therapeutics, diagnostics, and functional materials. Traditionally, their synthesis involved the use of thiols or derivatives, which are associated with unpleasant odors potential health risks. Recently, significant research has focused on employing oxygenated sulfur compounds, such as sulfinates, sulfonyl oxyacids, sulfoxides, thiol surrogates for thioether synthesis. This review highlights recent advancements deoxygenative synthesis, categorizing them by reaction types, including cross-coupling reactions, C–H functionalization, hydro/halo/oxy-thiolation unsaturated hydrocarbons. We also discuss representative mechanisms to provide comprehensive understanding these innovative approaches. 1 Introduction 2 Cross-Coupling Reactions 3 Functionalization 4 Hydro/Halo/Oxy-thiolation Unsaturated Hydrocarbons 5 Conclusion

Language: Английский

Citations

1

Towards a more Sustainable Photocatalysis using Copper and Iron DOI Creative Commons
Youssef Abderrazak, Oliver Reiser

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 100998 - 100998

Published: Jan. 1, 2025

Language: Английский

Citations

1

Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer DOI
Dan Yang,

Yu-Tong Mei,

Ziyi Guo

et al.

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

Published: Feb. 28, 2025

Carboxylic acids are bench-stable and readily available chemical feedstocks that function as optimal fundamental synthetic platforms for the construction of C(sp3)–C(sp3) bonds via decarboxylation processes. We present a novel practical protocol decarboxylative alkylation Morita–Baylis–Hillman acetates with various carboxylic photoinduced iron-mediated ligand-to-metal charge transfer (LMCT) process under redox-neutral conditions. This method exhibits remarkable tolerance to wide array acids, including primary, secondary, tertiary obviating requirement preactivated radical precursors. The preliminary mechanistic analyses indicate pathway is involved in this catalytic transformation.

Language: Английский

Citations

1

Iron-Catalyzed Photochemical Synthesis of Sulfinamides from Aliphatic Hydrocarbons and Sulfinylamines DOI

Guang-Da Xia,

Run Li, Long Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3703 - 3708

Published: April 26, 2024

An iron-catalyzed photochemical sulfinamidation of hydrocarbons with

Language: Английский

Citations

8

Aminomethylations of electron-deficient compounds—bringing iron photoredox catalysis into play DOI Creative Commons
Aleksandra Ilic,

Benjamin R. Strücker,

Catherine Johnson

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(30), P. 12077 - 12085

Published: Jan. 1, 2024

Electron transfer to the 2 LMCT state of a photoactive complex based on Earth-abundant iron has been used drive photocatalytic aminomethylation reactions by generation α-aminoalkyl radicals and underlying mechanism investigated.

Language: Английский

Citations

5

Light-induced ligand-to-metal charge transfer of Fe(III)-OR species in organic synthesis DOI

Jie Qin,

Hong Lei,

Chuanhua Gao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(30), P. 6034 - 6044

Published: Jan. 1, 2024

This review highlights studies on ligand-to-metal charge transfer of Fe( iii )-OR species in organic transformations.

Language: Английский

Citations

5

Iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light DOI

Arona Fall,

Mihaela Magdei,

Mariia Savchuk

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(49), P. 6316 - 6319

Published: Jan. 1, 2024

Eco-efficient LMCT based redox-neutral iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light.

Language: Английский

Citations

4

Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids DOI Creative Commons

Ilia Perov,

Karizza F. Catenza,

Alexandre Jose

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155507 - 155507

Published: Feb. 1, 2025

Language: Английский

Citations

0

Harnessing visible light for alkenylation reactions: A promising strategy in organic synthesis DOI

M. Manod,

Archana Vijayakumar,

TS Abhinav

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 579, P. 115028 - 115028

Published: March 22, 2025

Language: Английский

Citations

0

Iron‐Catalyzed, Light‐Driven Decarboxylative Alkoxyamination DOI Creative Commons

Milan Innocent,

Clément Tanguy,

Sigrid Gavelle

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(41)

Published: May 13, 2024

An iron-catalyzed visible-light driven decarboxylative alkoxyamination is disclosed. In the presence of FeBr

Language: Английский

Citations

3