4.8 Article

Visible Light-Mediated Cyclisation Reaction for the Synthesis of Highly-Substituted Tetrahydroquinolines and Quinolines

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Organic

Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines

Juulia Talvitie et al.

Summary: By using visible-light-excited 9,10-phenanthrenequinone (PQ*) as a photocatalyst, polysubstituted quinolines were successfully synthesized via the electrocyclization of 2-vinylarylimines. Experimental results showed that quantitative yields of 2,4-disubstituted quinolines could be obtained in a short period of time under blue LEDs excitation with the presence of MgCO3.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Photocatalytic Synthesis of Quinolines via Povarov Reaction under Oxidant-Free Conditions

Long-Long Su et al.

Summary: This paper describes an approach for synthesizing quinolines either from N-alkyl anilines or from anilines and aldehydes. A dual-catalyst system consisting of a photocatalyst and a proton reduction cocatalyst is used. Without the need for sacrificial oxidant and under mild conditions, the reactions can yield quinolines with excellent yields and produce H2 as a byproduct.

ORGANIC LETTERS (2022)

Review Chemistry, Multidisciplinary

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Laura Buglioni et al.

Summary: This paper provides a comprehensive overview of the exciting technological advances in the field of photoinduced chemical transformations, including flow chemistry, high-throughput experimentation, reactor design and scale-up, and the combination of photo- and electro-chemistry.

CHEMICAL REVIEWS (2022)

Article Chemistry, Multidisciplinary

Synthesis of Homoallylic Amines by Radical Allylation of Imines with Butadiene under Photoredox Catalysis

Yuqing Chen et al.

Summary: In this study, we present a metal-free radical cross-coupling strategy for the synthesis of homoallyl amines. This method involves the reaction between an alpha-amino alkyl radical and a transient allylic radical to obtain homoallyl amines from readily available materials. The method exhibits excellent regioselectivity and broad functional group compatibility.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Physical

The promise and pitfalls of photocatalysis for organic synthesis

Timothy Noel et al.

Summary: Progress in photocatalysis for organic synthesis has been rapidly advancing over the last 15 years, with an explosion of transformations enabled by visible light and the development of new reactor technologies and diverse photocatalysts. This perspective reflects on the achievements made, highlights the benefits of using photocatalysis in compound synthesis, and identifies critical challenges to be addressed as photocatalysis enters a new era of widespread adoption.

CHEM CATALYSIS (2022)

Review Chemistry, Multidisciplinary

The 2-Pyridyl Problem: Challenging Nucleophiles in Cross-Coupling Arylations

Xinlan A. F. Cook et al.

Summary: This review focuses on the methods developed for the challenging coupling of 2-pyridine nucleophiles with (hetero)aryl electrophiles, ranging from traditional cross-coupling processes to alternative nucleophilic reagents and novel main group approaches.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Biochemistry & Molecular Biology

Quinolines, a perpetual, multipurpose scaffold in medicinal chemistry

Pratibha Yadav et al.

Summary: Quinoline is a versatile pharmacophore with a wide range of pharmacological activities, and quinoline hybrids have shown promising anticancer, anti-inflammatory, antibacterial, and other activities. Numerous studies have summarized the recent advances of quinoline derivatives, helping in the development of clinically viable drug candidates for the treatment of incurable diseases.

BIOORGANIC CHEMISTRY (2021)

Article Chemistry, Applied

Development and Proof of Concept for a Large-Scale Photoredox Additive-Free Minisci Reaction

Mark A. Graham et al.

Summary: New route development activities for ceralasertib have led to the discovery of an efficient, acid additive-free, photoredox Minisci reaction. Mechanistic understanding and optimization of the catalyst system has significantly enhanced the reaction rate, with a large-scale continuous photoflow process providing promising proof-of-concept data for future clinical manufacture applications of ceralasertib.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2021)

Article Chemistry, Organic

Base-Promoted Tandem Synthesis of 2-Azaaryl Tetrahydroquinolines

Shuguang Chen et al.

Summary: A novel method for synthesizing 2-azaaryl tetrahydroquinolines is reported by the base-promoted tandem reaction of azaaryl methyl amines and styrene derivatives. Mechanistic probe experiments confirm the mechanism involving deprotonation of the benzylic C-H bond and addition to the styrene vinyl group via the SNAr mechanism. High yields of up to 95% were achieved in over 30 examples, demonstrating the potential applicability of this method.

ORGANIC LETTERS (2021)

Article Chemistry, Applied

Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines

Mikko K. Makela et al.

Summary: Oxidized active carbon catalyzes the formation of polysubstituted quinolines through a cascade manner involving condensation, electrocyclization, and dehydrogenation, allowing access to a wide range of quinolines. The metal-free catalytic procedure provides a heterogeneous protocol for the synthesis of various polysubstituted quinolines, with mechanistic studies indicating the importance of acid and quinoidic groups in oAC for the catalytic reaction.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines

J. Henry Blackwell et al.

Summary: An operationally straightforward multicomponent protocol for the synthesis of diverse alpha-trialkyl-alpha-tertiary amines was reported, utilizing visible-light-mediated photocatalysis with Ir(III) complexes. The reaction proceeds through a redox-neutral pathway, involving the photocatalytic redox-relay of imine intermediates. The presence of a benzylic amine component drives a hydrogen transfer step to close the photocatalytic cycle.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Enantioselective [2+2] Photocycloaddition via Iminium Ions: Catalysis by a Sensitizing Chiral Bronsted Acid

Franziska Pecho et al.

Summary: N,O-Acetals derived from alpha,beta-unsaturated beta-aryl substituted aldehydes and (1-aminocyclohexyl)methanol underwent a catalytic enantioselective [2 + 2] photocycloaddition to a variety of olefins with high yield and enantioselectivity under visible light irradiation using a chiral phosphoric acid as the catalyst. The formation of an iminium ion, the role of thioxanthone moieties, and the efficient enantioface differentiation were confirmed through NMR studies.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Review Chemistry, Multidisciplinary

Taming the excited state reactivity of imines - from non-radiative decay to aza Paterno-Buchi reaction

Sunil Kumar Kandappa et al.

Summary: This review discusses the excited state characteristics of imines and the processes governing their photochemical and photophysical properties, as well as pathways for deactivation and types of photochemical reactions. It also highlights recent strategies developed to address fundamental issues in the aza Paterno-Buchi reaction.

CHEMICAL SOCIETY REVIEWS (2021)

Review Chemistry, Multidisciplinary

Multi-Photon Excitation in Photoredox Catalysis: Concepts, Applications, Methods

Felix Glaser et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Organic

Visible Light Photocatalytic Synthesis of Tetrahydroquinolines Under Batch and Flow Conditions

Daniel Gonzalez-Munoz et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Biochemistry & Molecular Biology

Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs

Martin Kos et al.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2020)

Article Chemistry, Multidisciplinary

Regioselective/electro-oxidative intermolecular [3+2] annulation for the preparation of indolines

Qingqing Wang et al.

CHEMICAL SCIENCE (2020)

Review Biochemistry & Molecular Biology

Covalent inhibitors: a rational approach to drug discovery

Fandi Sutanto et al.

RSC MEDICINAL CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Visible-Light-Induced Organic Photochemical Reactions through Energy-Transfer Pathways

Quan-Quan Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Progress in the Chemistry of Tetrahydroquinolines

Isravel Muthukrishnan et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Streamlined Synthesis of C(sp3)-Rich N-Heterospirocycles Enabled by Visible-Light-Mediated Photocatalysis

Nils J. Floden et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

The Tandem Photoredox Catalysis Mechanism of [Ir(ppy)2(dtb-bpy)]+ Enabling Access to Energy Demanding Organic Substrates

Timothy U. Connell et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Organic

[6π] Photocyclization to cis-Hexahydrocarbazol-4-ones: Substrate Modification, Mechanism, and Scope

Sachin G. Modha et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

Iminium and enamine catalysis in enantioselective photochemical reactions

You-Quan Zou et al.

CHEMICAL SOCIETY REVIEWS (2018)

Article Chemistry, Organic

Diels-Alder Reactions with Ethylene and Superelectrophiles

Hien Vuong et al.

ORGANIC LETTERS (2018)

Article Chemistry, Multidisciplinary

Photocatalytic reverse polarity Povarov reaction

Jamie A. Leitch et al.

CHEMICAL SCIENCE (2018)

Article Biotechnology & Applied Microbiology

Expanding the medicinal chemistry synthetic toolbox

Jonas Bostrom et al.

NATURE REVIEWS DRUG DISCOVERY (2018)

Review Chemistry, Applied

Light on the Horizon: Current Research and Future Perspectives in Flow Photochemistry

Fabrizio Politano et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2018)

Article Chemistry, Multidisciplinary

Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals

Mattia Silvi et al.

NATURE CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Visible Light Photocatalysis of 6π Heterocyclization

Niels Munster et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Realizing an Aza Paterno-Buchi Reaction

Elango Kumarasamy et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Remote Aliphatic C-H Functionalizations through a 1,5-Hydrogen Transfer Cascade

Wei Shu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Electrocatalytic Generation of Amidyl Radicals for Olefin Hydroamidation: Use of Solvent Effects to Enable Anilide Oxidation

Lin Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Triiodide-Mediated δ-Amination of Secondary C-H Bonds

Ethan A. Wappes et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Chromoselective Photocatalysis: Controlled Bond Activation through Light-Color Regulation of Redox Potentials

Indrajit Ghosh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Organic Photoredox Catalysis

Nathan A. Romero et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Organic

Photoredox Catalysis in Organic Chemistry

Megan H. Shaw et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Synthesis of Quinolines: A Green Perspective

Vasco F. Batista et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2016)

Article Chemistry, Applied

Direct Synthesis of Hemiaminal Ethers via a Three-Component Reaction of Aldehydes, Amines and Alcohols

Alvaro Beltran et al.

ADVANCED SYNTHESIS & CATALYSIS (2015)

Article Chemistry, Multidisciplinary

Sodium Salts of Anionic Chiral Cobalt(III) Complexes as Catalysts of the Enantioselective Povarov Reaction

Jie Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions

Jacob Davies et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Medicinal

Rings in Drugs

Richard D. Taylor et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

Article Chemistry, Organic

SnAP Reagents for the Synthesis of Piperazines and Morpholines

Michael U. Luescher et al.

ORGANIC LETTERS (2014)

Review Chemistry, Multidisciplinary

Fundamental aspects of property tuning in push-pull molecules

Filip Bures

RSC ADVANCES (2014)

Review Chemistry, Multidisciplinary

Recent advances in the synthesis of quinolines: a review

Shraddha M. Prajapati et al.

RSC ADVANCES (2014)

Review Chemistry, Multidisciplinary

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

Christopher K. Prier et al.

CHEMICAL REVIEWS (2013)

Article Chemistry, Physical

Reversible trans-cis photoisomerization of new pyrrolidene heterocyclic imines

Paulo J. Coelho et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Oxygen Switch in Visible-Light Photoredox Catalysis: Radical Additions and Cyclizations and Unexpected C-C-Bond Cleavage Reactions

Shaoqun Zhu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Inorganic & Nuclear

Enhanced Luminescent Iridium(III) Complexes Bearing Aryltriazole Cyclometallated Ligands

Sebastien Ladouceur et al.

INORGANIC CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

Chiral Bronsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction

Hua Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Review Biochemistry & Molecular Biology

Quinoline, quinazoline and acridone alkaloids

Joseph P. Michael

NATURAL PRODUCT REPORTS (2007)

Article Chemistry, Multidisciplinary

Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction

Takahiko Akiyama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)