Photoinduced intermolecular hydrogen atom transfer reactions in organic synthesis

Chem Catalysis, Journal Year: 2021, Volume and Issue: 1(3), P. 523 - 598

Published: May 24, 2021

Language: Английский

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Scalable Photoelectrochemical Dehydrogenative Cross‐Coupling of Heteroarenes with Aliphatic C−H Bonds

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(34), P. 14275 - 14280

Published: June 3, 2020

Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic C-H bonds provides straightforward access to functionalized from readily available Established methods employ stoichiometric chemical oxidants under conditions heating or light irradiation. By merging electrochemistry photochemistry, we have achieved efficient photoelectrochemical dehydrogenative C(sp3 )-H donors through H2 evolution, without the addition metal catalysts oxidants. Mechanistically, donor is converted a nucleophilic carbon radical H-atom transfer chlorine atom, which produced by irradiation anodically generated Cl2 Cl- . The then undergoes substitution heteroarene afford alkylated products.

Language: Английский

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En Route to Intermolecular Cross-Dehydrogenative Coupling Reactions

The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 84(20), P. 12705 - 12721

Published: Aug. 23, 2019

Cross-coupling reaction between two C-H bonds has become a fundamental strategy in synthetic organic chemistry. With its increasing importance green chemistry, atom economy, and step development sky-rocketed within the last 20 years, with term "cross-dehydrogenative coupling (CDC)" popularized progressed by group of Li others to describe direct Y-Z bond formations from Y-H Z-H under oxidative conditions. Among all types CDC reactions, C-C are prime building up molecular complexity but their categorization currently remains disarray due wide diversity, resulting frequent display separate topics. In this Perspective, contemporary via activation strategies is presented herein, which could be vital for future designs. mechanism-based discussion, we wish that minireview will help more chemists gain insight into design reactions inspires ideas on topic.

Language: Английский

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Perspectives on green synthesis and catalysis

Green Synthesis and Catalysis, Journal Year: 2020, Volume and Issue: 1(1), P. 1 - 11

Published: June 1, 2020

Despite their impressive capacity to access diverse functional groups and synthesize structurally complex molecules, the majority of organic reactions suffers from harsh conditions, low atom economy, hazardous waste production. The goal our research is geared towards developing efficient methods minimize adverse environmental impact contributing chemical sustainability. Herein, we illustrate three distinct green approaches, studying novel reactivities with environmentally innocuous reagents improve synthetic efficiency, utilization natural feedstocks, employment energy facilitate various important transformations. From this perspective article, hope provide an overview chemistry inspire expansion field in future.

Language: Английский

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Visible light promoted cross-dehydrogenative coupling: a decade update

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(20), P. 6632 - 6681

Published: Jan. 1, 2020

In this review, all the visible light promoted cross-dehydrogenative coupling methodologies that have been developed over last decade are disclosed.

Language: Английский

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Cross-dehydrogenative coupling: a sustainable reaction for C–C bond formations

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(18), P. 6789 - 6862

Published: Jan. 1, 2021

We provide a review of the progress cross-dehydrogenative coupling reactions in constructing wide variety C–C bonds. Sustainable can be combined with multiple forms energy output.

Language: Английский

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A general electron donor–acceptor complex for photoactivation of arenes via thianthrenation

Chemical Science, Journal Year: 2022, Volume and Issue: 13(19), P. 5659 - 5666

Published: Jan. 1, 2022

General photoactivation of EDA complexes between arylsulfonium salts and 1,4-diazabicyclo[2.2.2]octane was discovered. This practical mode enables the generation aryl radicals for C–H functionalization arenes.

Language: Английский

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Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(18), P. 10253 - 10345

Published: Jan. 1, 2021

The chameleonic properties of oxygen accounts for the diverse reactivity O-functionalities and their profound role in organic synthesis.

Language: Английский

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Resurgence and advancement of photochemical hydrogen atom transfer processes in selective alkane functionalizations

Chemical Science, Journal Year: 2023, Volume and Issue: 14(25), P. 6841 - 6859

Published: Jan. 1, 2023

The selective functionalization of alkanes has long been recognized as a prominent challenge and an arduous task in organic synthesis. Hydrogen atom transfer (HAT) processes enable the direct generation reactive alkyl radicals from feedstock have successfully employed industrial applications such methane chlorination process,

Language: Английский

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Arylcarboxylation of unactivated alkenes with CO2 via visible-light photoredox catalysis

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: June 14, 2023

Photocatalytic carboxylation of alkenes with CO2 is a promising and sustainable strategy to synthesize high value-added carboxylic acids. However, it challenging rarely investigated for unactivated due their low reactivities. Herein, we report visible-light photoredox-catalyzed arylcarboxylation CO2, delivering variety tetrahydronaphthalen-1-ylacetic acids, indan-1-ylacetic indolin-3-ylacetic chroman-4-ylacetic acids thiochroman-4-ylacetic in moderate-to-good yields. This reaction features chemo- regio-selectivities, mild conditions (1 atm, room temperature), broad substrate scope, good functional group compatibility, easy scalability facile derivatization products. Mechanistic studies indicate that situ generation carbon dioxide radical anion following addition might be involved the process.

Language: Английский

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