Visible Light-Promoted β-Functionalization of Carbonyl Compounds in the Presence of Organic Dyes DOI Creative Commons
Luigi Dolcini, Tommaso Gandini,

Riccardo Castiglioni

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(20), С. 14283 - 14291

Опубликована: Окт. 4, 2023

Herein, we investigate the use of organic photocatalysts in visible light-promoted β-functionalization carbonyl compounds. In particular, studied addition aliphatic aldehydes to α,β-unsaturated compounds (β-Michael addition), and reaction cyclic ketones with either (β-aldol condensation) or imines (β-Mannich reaction). Among dyes tested, donor–acceptor cyanoarenes gave best results, promoting transformations interest moderate good yields. The scope was investigated on substrates different steric electronic properties. Fluorescence quenching analysis (Stern–Volmer experiments) led us propose for these reactions a reductive mechanism involving transient 5πe– activation mode.

Язык: Английский

Metallaphotoredox catalysis for sp3C–H functionalizations through hydrogen atom transfer (HAT) DOI
Jingchang Zhang, Magnus Rueping

Chemical Society Reviews, Год журнала: 2023, Номер 52(12), С. 4099 - 4120

Опубликована: Янв. 1, 2023

sp 3 C–H functionalizations under the combination of photocatalytic HAT and transition metal catalysis.

Язык: Английский

Процитировано

94

The green chemistry paradigm in modern organic synthesis DOI
Sergei G. Zlotin, Ksenia S. Egorova, Valentine P. Ananikov

и другие.

Russian Chemical Reviews, Год журнала: 2023, Номер 92(12), С. RCR5104 - RCR5104

Опубликована: Дек. 1, 2023

After the appearance of green chemistry concept, which was introduced in vocabulary early 1990s, its main statements have been continuously developed and modified. Currently, there are 10–12 cornerstones that should form basis for an ideal chemical process. This review analyzes accumulated experience achievements towards design products processes reduce or eliminate use generation hazardous substances. The presents views leading Russian scientists specializing various fields this subject, including homogeneous heterogeneous catalysis, fine basic organic synthesis, electrochemistry, polymer chemistry, based on bio-renewable feedstocks energetic compounds materials. A new approach to quantitative evaluation environmental friendliness by authors is described. <br> bibliography includes 1761.

Язык: Английский

Процитировано

41

Metallaphotoredox catalysis for sp3 C–H functionalizations through single-electron transfer DOI
Jingchang Zhang, Magnus Rueping

Nature Catalysis, Год журнала: 2024, Номер 7(9), С. 963 - 976

Опубликована: Сен. 24, 2024

Язык: Английский

Процитировано

7

Basic Concepts and Activation Modes in Visible-Light-Photocatalyzed Organic Synthesis DOI
Karthik Gadde, Dries De Vos, Bert U. W. Maes

и другие.

Synthesis, Год журнала: 2022, Номер 55(02), С. 164 - 192

Опубликована: Авг. 29, 2022

Abstract Visible light photocatalysis has established itself as a promising sustainable and powerful strategy to access reactive intermediates, i.e. radicals radical ions, under mild reaction conditions using visible irradiation. This field enables the development of formerly challenging or even previously inaccessible organic transformations. In this tutorial review, an overview essential concepts techniques visible-light-mediated chemical processes most common types photochemical activation molecules, photoredox catalysis photosensitization, are discussed. Selected photocatalytic alkene functionalization reactions included examples illustrate basic with particular attention given understanding their mechanisms. 1 Introduction 2 Photocatalysts 3 Photophysical Electrochemical Properties 3.1 Excited-State Energy 3.2 Ground-State Redox Potentials 3.3 3.4 Local Absorbance Maximum for Lowest Absorption 3.5 Lifetime 3.6 [Ru(bpy)3]2+ Case Study 3.7 Basic Laws Equations Photochemistry Photocatalysis 3.8 Common Terminology in 4 Activation Modes 4.1 Photoinduced Electron Transfer 4.2 5 Conclusions Outlook

Язык: Английский

Процитировано

25

Emerging Activation Modes and Techniques in Visible-Light-Photocatalyzed Organic Synthesis DOI
Dries De Vos, Karthik Gadde, Bert U. W. Maes

и другие.

Synthesis, Год журнала: 2022, Номер 55(02), С. 193 - 231

Опубликована: Сен. 16, 2022

Abstract Visible light photocatalysis has evolved into a promising mild and sustainable strategy to access radicals. This field unlocks formerly challenging or even previously inaccessible organic transformations. In this review, an overview of some lesser-known modes photochemical activation molecules several emerging techniques within the versatile visible are discussed. These illustrated by selected photocatalytic reactions, with particular attention given reaction mechanism. 1 Introduction 2 Advanced Photoactivation Modes 2.1 Photoinduced Hydrogen-Atom Transfer 2.2 Proton-Coupled Electron 2.3 Donor-Acceptor Organic Substrates 2.4 Excited-State Transition Metal Catalysis 3 Emerging Techniques 3.1 Dual 3.2 Excited Radical Ion Photocatalysis 3.3 Upconversion Strategies Other Two-Photon Mechanisms 3.4 Red Near-Infrared 4 Conclusions Outlook

Язык: Английский

Процитировано

20

Ni‐Catalyzed/mediated C−X (X=N, O, S) Bond Formation Chelation‐Assisted by Bidentate Directing Groups DOI
Peng Xu, Shengxian Zhao

ChemistrySelect, Год журнала: 2024, Номер 9(5)

Опубликована: Янв. 29, 2024

Abstract Recently, transition‐metal‐catalyzed C−H functionalization has attracted significant attention due to its potential applications in different fields. Among metals, nickel is regarded as a more sustainable 3d‐transition metal, which been widely explored. Therefore, this review focuses on the recent advances field of nickel‐catalyzed assisted with bidentate directing groups (DGs) construct C−X (N, S, O) bond. The latest advancement catalysed bond are reviewed and covers literatures from 2015–2022. In addition, substrate scope limitations well partial mechanism discussed.

Язык: Английский

Процитировано

1

Green light-mediated dual eosin Y/PdII-catalyzed C(sp2)–H arylation of N–H unprotected 2-arylquinazolinones DOI
Shuvam Mondal, Ranjan Jana

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(27), С. 5540 - 5545

Опубликована: Янв. 1, 2024

An eosin Y/Pd II dual catalytic highly regio- and chemoselective C(sp 2 )–H monoarylation of N–H unprotected 2-phenyl quinazolinones with diazonium salts under visible light irradiation is disclosed.

Язык: Английский

Процитировано

1

Visible Light-Promoted β-Functionalization of Carbonyl Compounds in the Presence of Organic Dyes DOI Creative Commons
Luigi Dolcini, Tommaso Gandini,

Riccardo Castiglioni

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(20), С. 14283 - 14291

Опубликована: Окт. 4, 2023

Herein, we investigate the use of organic photocatalysts in visible light-promoted β-functionalization carbonyl compounds. In particular, studied addition aliphatic aldehydes to α,β-unsaturated compounds (β-Michael addition), and reaction cyclic ketones with either (β-aldol condensation) or imines (β-Mannich reaction). Among dyes tested, donor–acceptor cyanoarenes gave best results, promoting transformations interest moderate good yields. The scope was investigated on substrates different steric electronic properties. Fluorescence quenching analysis (Stern–Volmer experiments) led us propose for these reactions a reductive mechanism involving transient 5πe– activation mode.

Язык: Английский

Процитировано

3