Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu2O–CeO2/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction DOI
Ganesh Sunil More, Ashish Kumar Kar, Rajendra Srivastava

et al.

Inorganic Chemistry, Journal Year: 2022, Volume and Issue: 61(47), P. 19010 - 19021

Published: Nov. 14, 2022

The development of an economical transition metal-based catalyst for photocatalytic carbon-carbon coupling reactions is aspiring. Herein, a Cu-Ce metal-organic framework (MOF) was synthesized and carbonized to produce bimetallic Cu2O-CeO2/C, which utilized in the Sonogashira cross-coupling reaction. defects oxygen vacancies were characterized by X-ray photoelectron spectroscopy Raman spectroscopy, while nature Cu H2-TPR analysis. defect-induced MOF-derived heterojunction created more (OV) CeO2, revealing high activity. (Cu2O-CeO2/C) formed Cu(I)-phenylacetylide active complex exhibited higher catalytic activity visible light-induced 25%Cu2O-CeO2/C offered 93.8% phenylacetylene conversion with 94.2% product selectivity using household light-emitting diodes. No discernible loss observed from recycling catalyst. Based on activity, control reactions, physicochemical optoelectronic characterization, structure-activity relationship established reaction mechanism proposed. Replacement costly Pd cheap Cu2O-CeO2-based synthesis commercially important compounds sustainable process will be highly attractive chemists industrialists.

Language: Английский

Photocatalytic Late-Stage C–H Functionalization DOI
Peter Bellotti, Huan‐Ming Huang,

Teresa Faber

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(8), P. 4237 - 4352

Published: Jan. 24, 2023

The emergence of modern photocatalysis, characterized by mildness and selectivity, has significantly spurred innovative late-stage C–H functionalization approaches that make use low energy photons as a controllable source. Compared to traditional strategies, photocatalysis paves the way toward complementary and/or previously unattainable regio- chemoselectivities. Merging compelling benefits with workflow offers potentially unmatched arsenal tackle drug development campaigns beyond. This Review highlights photocatalytic strategies small-molecule drugs, agrochemicals, natural products, classified according targeted bond newly formed one. Emphasis is devoted identifying, describing, comparing main mechanistic scenarios. draws critical comparison between established ionic chemistry photocatalyzed radical-based manifolds. aims establish current state-of-the-art illustrate key unsolved challenges be addressed in future. authors aim introduce general readership functionalization, specialist practitioners evaluation methodologies, potential for improvement, future uncharted directions.

Language: Английский

Citations

324

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds DOI
Fanyang Mo, Di Qiu, Lei Zhang

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(10), P. 5741 - 5829

Published: April 9, 2021

Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance aryl spanning most disciplines chemical sciences, we review recent development chemistry over past seven years (2013-2020). Special emphasis is put on various new transformations involving generation radical intermediates via thermal, photochemical, and electrochemical means. Recent advances transition metal-catalyzed reactions using also reviewed. Together, these newly developed significantly expand synthetic chemist's repertoire aromatic carbon-carbon carbon-heteroatom bond forming methods precursors, providing powerful tools for synthesis modification complex molecular scaffolds.

Language: Английский

Citations

239

Photoredox‐Mediated Net‐Neutral Radical/Polar Crossover Reactions DOI
Rebecca J. Wiles,

Gary A. Molander

Israel Journal of Chemistry, Journal Year: 2020, Volume and Issue: 60(3-4), P. 281 - 293

Published: Feb. 18, 2020

Abstract Radical/Polar Crossover (RPC) chemistry is a rapidly growing subset of photoredox catalysis that characterized by transformations featuring both radical and ionic modes reactivity. Net‐neutral RPC particularly interesting in the single‐electron oxidation reduction steps occur through interaction with photocatalyst, thus precluding need for exogenous oxidants or reductants. As such, these facilitate rapid incorporation molecular complexity while maintaining mild reaction conditions. This review covers recent advances photoredox‐mediated net‐neutral synthetic methods, particular emphasis on C–C bond‐forming reactions.

Language: Английский

Citations

166

Visible light-driven C–H arylation of heteroarenes with aryl diazonium salts in water catalyzed by a Z-scheme CuInS2/K-C3N4 heterojunction DOI
Qian-Hui Liu,

S. K. KANG,

Zhen‐Shui Cui

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4803 - 4810

Published: Jan. 1, 2024

Z-scheme CuInS 2 /K-C 3 N 4 heterojunction has been designed and confirmed as efficient heterogeneous photocatalyst for arylation of heteroarenes with aryl diazonium salts in water under visible light irradiation to give arylated high yields.

Language: Английский

Citations

17

Flow Photochemistry as a Tool in Organic Synthesis DOI Creative Commons
Thomas H. Rehm

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(71), P. 16952 - 16974

Published: May 19, 2020

Abstract Photochemical transformations of molecular building blocks have become an important and widely recognized research field in the past decade. Detailed deep understanding novel photochemical catalysts reaction concepts with visible light as energy source has enabled a broad application portfolio for synthetic organic chemistry. In parallel, continuous‐flow chemistry microreaction technology basis thinking doing fashion clear focus on improved process control higher conversion selectivity. As can be seen by large number scientific publications flow photochemistry recent past, both topics found each other exceptionally well‐suited counterparts high synergy combining technology. This review will give overview selected classes, which represent chemistry, benefit from mild defined conditions transfer batch to mode.

Language: Английский

Citations

122

A Need for Caution in the Preparation and Application of Synthetically Versatile Aryl Diazonium Tetrafluoroborate Salts DOI Open Access
James D. Firth, Ian J. S. Fairlamb

Organic Letters, Journal Year: 2020, Volume and Issue: 22(18), P. 7057 - 7059

Published: Aug. 28, 2020

ADVERTISEMENT RETURN TO ISSUEEditorialNEXTA Need for Caution in the Preparation and Application of Synthetically Versatile Aryl Diazonium Tetrafluoroborate SaltsJames D. FirthJames FirthDepartment Chemistry, University York, Heslington, York YO10 5DD, U.K.More by James Firthhttp://orcid.org/0000-0003-2283-552X Ian J. S. Fairlamb*Ian FairlambDepartment U.K.*Email: [email protected]More Fairlambhttp://orcid.org/0000-0002-7555-2761Cite this: Org. Lett. 2020, 22, 18, 7057–7059Publication Date (Web):August 28, 2020Publication History Received11 August 2020Published online28 inissue 18 September 2020https://pubs.acs.org/doi/10.1021/acs.orglett.0c02685https://doi.org/10.1021/acs.orglett.0c02685editorialACS PublicationsCopyright © 2020 American Chemical Society. This publication is available under these Terms Use. Request reuse permissions free to access through this site. Learn MoreArticle Views19973Altmetric-Citations77LEARN ABOUT THESE METRICSArticle Views are COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing article, calculated Crossref daily. Find more information about citation counts.The Altmetric Attention Score a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail (640 KB) Get e-AlertscloseSUBJECTS:Anions,Explosives,Materials,Organic reactions,Salts e-Alerts

Language: Английский

Citations

101

A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry DOI Creative Commons
Timothée Constantin, Fabio Juliá, Nadeem S. Sheikh

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(47), P. 12822 - 12828

Published: Jan. 1, 2020

Aminoalkyl radicals can be used as both initiators and chain-carriers for the conversion of aryl halides into corresponding radicals. This approach by-passes requirement strongly reducing photocatalysts.

Language: Английский

Citations

100

Recent Methodologies That Exploit Oxidative Addition of C–N Bonds to Transition Metals DOI
Javier García‐Cárceles, Karim A. Bahou, John F. Bower

et al.

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(21), P. 12738 - 12759

Published: Oct. 19, 2020

The activation of σ-bonds by transition metals underpins a wide range methods for the synthesis complex molecules. Within this context, C–N bond has emerged recently as powerful strategy preparation or utilization nitrogen-containing compounds, due to prevalence bonds in organic compounds. A key challenge area is that most are relatively inert, and makes their difficult task. Since turn millennium number published articles regarding grown exponentially, providing important improvements methodologies such transformations. Indeed, several distinct strategies have been developed achieve activation. common exploited either strain release quaternization nitrogen center, while other state-of-the-art strategies, oxidative addition neutral use directing groups, also appeared. Despite considerable progress, deeper insight into mechanisms atom economy still required field advance. In Perspective we give an overview advances catalytic where achieved metals.

Language: Английский

Citations

94

Recent advances in using 4DPAIPN in photocatalytic transformations DOI
Praveen P. Singh, Vishal Srivastava

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 19(2), P. 313 - 321

Published: Nov. 19, 2020

1,3-Dicyano-2,4,5,6-tetrakis(diphenylamino)-benzene has emerged as a powerful and attractive metal-free organophotocatalyst for organic transformation is expected to contribute great extent toward the advancement development of synthetic methodologies.

Language: Английский

Citations

93

Recent application of visible-light induced radicals in C–S bond formation DOI Creative Commons
Vishal Srivastava, Pravin K. Singh, Arjita Srivastava

et al.

RSC Advances, Journal Year: 2020, Volume and Issue: 10(34), P. 20046 - 20056

Published: Jan. 1, 2020

The sulphur centered radicals, produced from various organic compounds, in high efficiency by single-electron-transfer (SET) oxidation.

Language: Английский

Citations

79