Recent advances in photoorganocatalysis (2019–2023) DOI
Petros L. Gkizis, Christoforos G. Kokotos

Royal Society of Chemistry eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 199 - 236

Published: Dec. 18, 2024

From 2008 until now, the advent of photochemistry has offered a plethora synthetic opportunities to chemists worldwide. The ability light generate reactive species under mild reaction conditions provided access unexplored pathways. Lately, development photochemical reactions employing small organic molecules as catalysts increased. Serving basic principles Green Chemistry, have proven be an excellent alternative use metal-based complexes, performing elegant transformations. Their is based on their mediate events, such Single Electron Transfer (SET), Energy (EnT) and Hydrogen Atom (HAT). Furthermore, there been reports capability form Donor–Acceptor (EDA) complexes facilitating challenging Herein, we will focus promoted by during last 5 years (2019–2023).

Language: Английский

Chemodivergent dearomatization of benzene-linked O-oxime esters via EnT-induced radical cross-coupling DOI Creative Commons
Guohui Zeng,

Dongwen Guo,

Huanfeng Jiang

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Radical-mediated dearomatization strategies offer a blueprint for building value-added and synthetically valuable three-dimensional skeletons from readily available aromatic starting materials.

Language: Английский

Citations

0
Unification of Ru and carbon support in catalytic aqueous 1,6-hexanediol amination DOI

Phillip Palenicek,

Hafila S. Khairun,

Navneet Kumar Gupta

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 578, P. 115030 - 115030

Published: March 20, 2025

Language: Английский

Citations

0
Development of N-centered radical scavengers that enables photoredox-catalyzed transition-metal-free radical amination of alkyl pinacol boronates DOI Creative Commons
Changlei Zhu, Jiaxin Lin, Xiaoguang Bao

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 4, 2025

In recent years, amination of alkylboronates through ionic copper catalysis or boron-ate complex 1,2-metalation has been well established, but complementary radical processes remain less studied before. Herein, based on rational design, we develop several imine-type N-centered scavengers and apply them to the alkylboronates. The reaction proceeds under mild photoredox-catalyzed transition-metal-free conditions features excellent functional group tolerance. It also enables preparation a range medicinally valuable amine derivatives from natural products. Further application this reagent in C-H amination, deoxygenative decarboxylative three component trifluoromethylative/sulfonylative aminations are realized. mechanistic studies DFT calculations conducted provide detailed evidence for mechanism.

Language: Английский

Citations

0
Red Light and Supersilane: A Novel Pathway for Hydrofunctionalizations and Giese Reactions DOI Creative Commons
Aakanksha Gurawa, Marc Taillefer, Alexis Prieto

et al.

ACS Organic & Inorganic Au, Journal Year: 2025, Volume and Issue: 5(3), P. 221 - 227

Published: May 10, 2025

Herein, we describe the photoredox activation of silanes under deep-red irradiation with or without osmium-based photocatalysts to generate silyl radicals. These radicals were further employed for achieving various reactivities previously unexplored in red-light spectral region, such as hydrosilylation, hydrosulfonylation, and Giese reaction. Overall, developed protocols allow preparation a diverse array high-value molecules.

Language: Английский

Citations

0
Photocatalyzed Formation of gem‐Difluoroalkenes Using Oxime Esters DOI
Lilian Geniller, Marc Taillefer, Eric Clot

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(16), P. 3430 - 3437

Published: April 10, 2024

Abstract In this manuscript a general photocatalytic approach for the synthesis of alkyl‐substituted gem ‐difluoroalkenes using readily available oxime esters and 1‐bromo‐1,1‐difluoroprop‐2‐ene (BDFP) has been established. This strategy involving radical bromo elimination provides access to large variety value‐added fluorinated molecules. The mild reaction conditions are compatible with many functional groups including complex natural products or drug Experimental theoretical mechanistic investigations indicate that efficiency process relies on crucial role imine radical, which is formed after photoexcitation via energy transfert (EnT) decarboxylation ester. Indeed, would either behave as bromine scavenger an XAT promoter in reaction.

Language: Английский

Citations

2
Metal‐Free Decarboxylative Allylation of Oxime Esters under Light Irradiation DOI Creative Commons
Lilian Geniller,

Hiba Ben Kraim,

Eric Clot

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: May 24, 2024

Allylation reactions, often used as a key step for constructing complex molecules and drug candidates, typically rely on transition-metal (TM) catalysts. Even though TM-free radical allylations have been developed using allyl-stannanes, -sulfides, -silanes or -sulfones, much less procedures reported simple commercially available allyl halides, that are the preparation of before-mentioned derivatives. Here, we present straightforward photocatalytic protocol decarboxylative allylation oxime esters bromide derivatives under metal-free mild conditions. This methodology yields diverse variety functionalized including several pharmaceutically relevant molecules.

Language: Английский

Citations

2
Light-assisted functionalization of aryl radicals towards metal-free cross-coupling DOI
Huaibo Zhao,

Valentina Dafnae Cuomo,

Wei Tian

et al.

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 15, 2024

Language: Английский

Citations

1
Recent advances in photoorganocatalysis (2019–2023) DOI
Petros L. Gkizis, Christoforos G. Kokotos

Royal Society of Chemistry eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 199 - 236

Published: Dec. 18, 2024

From 2008 until now, the advent of photochemistry has offered a plethora synthetic opportunities to chemists worldwide. The ability light generate reactive species under mild reaction conditions provided access unexplored pathways. Lately, development photochemical reactions employing small organic molecules as catalysts increased. Serving basic principles Green Chemistry, have proven be an excellent alternative use metal-based complexes, performing elegant transformations. Their is based on their mediate events, such Single Electron Transfer (SET), Energy (EnT) and Hydrogen Atom (HAT). Furthermore, there been reports capability form Donor–Acceptor (EDA) complexes facilitating challenging Herein, we will focus promoted by during last 5 years (2019–2023).

Language: Английский

Citations

0