Dioxygen compatible electron donor-acceptor catalytic system and its enabled aerobic oxygenation DOI Creative Commons
Jialiang Wei,

Junhong Meng,

Caifang Zhang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Feb. 29, 2024

Abstract The photochemical properties of Electron Donor-Acceptor (EDA) complexes present exciting opportunities for synthetic chemistry. However, these strategies often require an inert atmosphere to maintain high efficiency. Herein, we develop EDA complex photocatalytic system through rational design, which overcomes the oxygen-sensitive limitation traditional systems and enables aerobic oxygenation reactions dioxygen activation. mild oxidation transfers electrons from donor effective catalytic acceptor upon visible light irradiation, are subsequently captured by molecular oxygen form superoxide radical ion, as demonstrated specific fluorescent probe, dihydroethidine (DHE). Furthermore, this visible-light mediated oxidative protocol is successfully applied in boronic acids. We believe that activation strategy enabled not only provides a practical approach but also promotes design application photocatalysis under ambient conditions.

Language: Английский

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis DOI
Nicholas E. S. Tay, Dan Lehnherr, Tomislav Rovis

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2487 - 2649

Published: Nov. 9, 2021

Redox processes are at the heart of synthetic methods that rely on either electrochemistry or photoredox catalysis, but how do and catalysis compare? Both approaches provide access to high energy intermediates (e.g., radicals) enable bond formations not constrained by rules ionic 2 electron (e) mechanisms. Instead, they 1e mechanisms capable bypassing electronic steric limitations protecting group requirements, thus enabling chemists disconnect molecules in new different ways. However, while providing similar intermediates, differ several physical chemistry principles. Understanding those differences can be key designing transformations forging disconnections. This review aims highlight these similarities between comparing their underlying principles describing impact electrochemical photochemical methods.

Language: Английский

Citations

357

Alkoxy Radicals See the Light: New Paradigms of Photochemical Synthesis DOI
Liang Chang, Qing An, Lingfei Duan

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2429 - 2486

Published: Oct. 6, 2021

Alkoxy radicals are highly reactive species that have long been recognized as versatile intermediates in organic synthesis. However, their development has impeded due to a lack of convenient methods for generation. Thanks advances photoredox catalysis, enabling facile access alkoxy from bench-stable precursors and free alcohols under mild conditions, research interest this field renewed. This review comprehensively summarizes the recent progress radical-mediated transformations visible light irradiation. Elementary steps radical generation either or central reaction development; thus, each section is categorized discussed accordingly. Throughout review, we focused on different mechanisms well impact synthetic utilizations. Notably, catalytic abundant still early stage, providing intriguing opportunities exploit diverse paradigms.

Language: Английский

Citations

290

Multicomponent Reductive Cross‐Coupling of an Inorganic Sulfur Dioxide Surrogate: Straightforward Construction of Diversely Functionalized Sulfones DOI

Yingying Meng,

Ming Wang, Xuefeng Jiang

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 59(3), P. 1346 - 1353

Published: Oct. 31, 2019

Abstract Conventionally, sulfones are prepared by oxidation of sulfides with strong oxidants. Now, a multicomponent reductive cross‐coupling involving an inorganic salt (sodium metabisulfite) for the straightforward construction is disclosed. Both intramolecular and intermolecular cross‐couplings were comprehensively explored, diverse accessible from corresponding alkyl aryl halides. Intramolecular cyclic systematically obtained five‐ to twelve‐membered rings. Naturally occurring aliphatic systems, such as steroids, saccharides, amino acids, highly compatible SO 2 ‐insertion cross‐coupling. Four clinically applied drug molecules, which include multiple heteroatoms functional groups active hydrogens, successfully via late‐stage insertion. Mechanistic studies show that radicals sulfonyl both involved intermediates in this transformation.

Language: Английский

Citations

191

α-Fe2O3 as a versatile and efficient oxygen atom transfer catalyst in combination with H2O as the oxygen source DOI
Yukun Zhao, Chaoyuan Deng, Daojian Tang

et al.

Nature Catalysis, Journal Year: 2021, Volume and Issue: 4(8), P. 684 - 691

Published: Aug. 9, 2021

Language: Английский

Citations

181

Molecular oxygen-mediated oxygenation reactions involving radicals DOI
Conghui Tang, Xu Qiu, Zengrui Cheng

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(14), P. 8067 - 8101

Published: Jan. 1, 2021

Molecular oxygen as a green, inexpensive oxidant and source has displayed lots of advantages compared to other oxidants. This review introduces the recent advances radical processes in molecular oxygen-mediated oxygenation reactions.

Language: Английский

Citations

165

Prospects and Challenges in Organosulfur Chemistry DOI
Ming Wang, Xuefeng Jiang

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(2), P. 671 - 677

Published: Jan. 3, 2022

Sulfur-containing molecules are increasingly crucial in chemistry-related fields and widely applied life science, material food pharmaceutical science. This perspective focuses on the introduction of green sulfurizing reagents sustainable methodologies to realize diverse kinds functionalized transformations synthetic applications. The text is organized according structure sulfur-containing corresponding method. It expected be interest organic chemistry professionals who wish better understand insights applications organosulfur transformations.

Language: Английский

Citations

136

An updated status and trends in actinide metal-organic frameworks (An-MOFs): From synthesis to application DOI
Kai Lv, Sebastian Fichter,

Mei Gu

et al.

Coordination Chemistry Reviews, Journal Year: 2021, Volume and Issue: 446, P. 214011 - 214011

Published: July 8, 2021

Language: Английский

Citations

116

Aerobic Photocatalysis: Oxidation of Sulfides to Sulfoxides DOI

Elpida Skolia,

Petros L. Gkizis,

Chistoforos G. Kokotos

et al.

ChemPlusChem, Journal Year: 2022, Volume and Issue: 87(4)

Published: Feb. 15, 2022

Sulfoxides constitute one of the most important functional groups in organic chemistry found numerous pharmaceuticals and natural products. are usually obtained from oxidation corresponding sulfides. Among various oxidants, oxygen or air considered greenest sustainable reagent. Photochemistry photocatalysis is increasingly applied new, as well traditional, yet demanding, reaction, like aerobic sulfides to sulfoxides, since has provided means access them mild effective ways. In this review, we will summarize photochemical protocols that have been developed for employing oxidant. The aim review present: i) a historical overview, ii) key mechanistic studies proposed mechanisms iii) categorize different catalytic systems literature.

Language: Английский

Citations

72

Photochemical aerobic oxidation of sulfides to sulfoxides: the crucial role of wavelength irradiation DOI Creative Commons

Elpida Skolia,

Petros L. Gkizis,

Nikolaos F. Nikitas

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(10), P. 4108 - 4118

Published: Jan. 1, 2022

Introducing green and sustainable photochemical aerobic protocols for the oxidation of sulfides to sulfoxides.

Language: Английский

Citations

70

Degradation of plastic wastes to commercial chemicals and monomers under visible light DOI
Jiaolong Meng, Yilin Zhou,

Daoji Li

et al.

Science Bulletin, Journal Year: 2023, Volume and Issue: 68(14), P. 1522 - 1530

Published: June 26, 2023

Language: Английский

Citations

56