☆ 4.8 Article

Synthesis of spiroquinolines through a one-pot multicatalytic and multicomponent cascade reaction

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷 47, 期 37, 页码 7044-7047

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.200802582

关键词

cyclization; homogeneous catalysis; multicomponent; reactions; platinum; quinolines

类别

Chemistry, Multidisciplinary

向作者/读者索取更多资源

Protocol

Reagent

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Review Chemistry, Multidisciplinary

Homogeneous Gold-Catalyzed Oxidation Reactions

Zhitong Zheng, Xu Ma, Xinpeng Cheng, Ke Zhao, Kaylaa Gutman, Tianyou Li, Liming Zhang

Summary: Homogeneous gold catalysis has seen significant development since the turn of the millennium, with oxidative gold catalysis being a vibrant subfield delivering valuable synthetic methods. This comprehensive review covers the mechanistic aspects, oxidants, and synthetic applications of oxidative gold catalysis.

CHEMICAL REVIEWS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Media-Driven Pd-Catalyzed Reaction Cascades with 1,3-Diynamides Leading Selectively to Either Indoles or Quinolines

Illia Lenko, Alexander Mamontov, Carole Alayrac, Remi Legay, Bernhard Witulski

Summary: The research demonstrates the divergent Pd-catalyzed reaction cascades with various 1,3-diynamides, leading to different products depending on the presence or absence of TBAF. Furthermore, deuterium labeling experiments reveal the unique formation mechanism of the products.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Organic

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

Juulia Talvitie, Iida Alanko, Evgeny Bulatov, Juho Koivula, Topias Pollanen, Juho Helaja

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)

添加到收藏夹

Article Chemistry, Organic

Palladium(ii)-catalyzed three-component tandem reactions: synthesis of multiply substituted quinolines

Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li

Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.

ORGANIC CHEMISTRY FRONTIERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Intraligand Charge Transfer Enables Visible-Light-Mediated Nickel-Catalyzed Cross-Coupling Reactions

Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber

Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Review Chemistry, Physical

An Overview of Catalytic Carbonylative Double Cyclization Reactions

Bartolo Gabriele, Raffaella Mancuso, Nicola Della Ca, Lucia Veltri, Ida Ziccarelli

Summary: This article provides an overview of catalytic carbonylative double cyclization reactions, where organic substrates and carbon monoxide are sequentially activated to form two new cycles with the incorporation of carbon monoxide. It highlights the power of this synthetic methodology in the one-step synthesis of complex molecular architectures using readily available CO as the building block. The review is divided into five sections: Introduction, Functionalized Olefinic Substrates, Functionalized Acetylenic Substrates, Functionalized Halides, and Conclusions and Future Perspectives.

CATALYSTS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Titanocene-Catalyzed [2+2] Cycloaddition of Bisenones and Comparison with Photoredox Catalysis and Established Methods

Zhenhua Zhang, Julius B. Stueckrath, Stefan Grimme, Andreas Gansaeuer

Summary: Cp2Ti(TFA) is a versatile catalyst for the [2+2] cycloaddition of bisenones through inner-sphere electron transfer, with a unique 5-exo step as the rate-determining step followed by a favorable 4-exo cyclization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Applied

Copper(I)-Catalyzed Intramolecular Cyclization of o-Propargyloxy Diketopiperazines to Access Diverse Diazabicyclic and Spiro-Diketopiperazinochromanes

Bita Manavi, Hossein Zahedian Tejeneki, Frank Rominger, Mahsa Armaghan, Walter Frank, Hamid Reza Bijanzadeh, Saeed Balalaie

Summary: This report discusses two distinctive intramolecular cyclizations of o-propargyloxy diketopiperazines achieved via a copper(I)-catalyzed reaction, offering an opportunity for the synthesis of challenging Diazabicyclics and Spiro-Diketopiperazinochromanes with high yields and exclusive diastereoselectivity.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Organic

Manganese-Catalysed Transfer Hydrogenation of Quinolines under Mild Conditions

Xiaoxiao Chu, Guoren Zhou, Maofu Pang, Hongwu Zhang

Summary: Here, an efficient method for the homogeneous manganese-catalysed transfer hydrogenation of N-heterocycles using ammonia-borane as a hydrogen source under mild reaction conditions is reported. The use of a PNP manganese pincer complex allows for good to excellent isolated yields. The reaction proceeds through the detection of 1,2-dihydroquinoline as an intermediate by NMR spectra analysis and deuterium labelling experiment.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Tetradehydro-Diels-Alder Reactions of Flexible Arylalkynes via Folding Inside a Molecular Cage

Georgi R. Genov, Hiroki Takezawa, Harumi Hayakawa, Makoto Fujita

Summary: The TDDA reaction is a useful method to assemble complex molecular structures from simple precursors in a single step, but it requires careful design of substrates and harsh reaction conditions. In this study, we demonstrate an efficient and site-selective TDDA transformation within a self-assembled Pd6L4 cage. The encapsulation of substrates within the large cavity of the cage allows for enhanced cyclization rates and high selectivity for unsymmetrical substrates.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Applied

Palladium-Catalyzed Hydroarylation of Homopropargyl Iodoindoles with Concurrent Alkyl and Iodonium Migrations

Irene Martin, Cristina Aragoncillo, Pedro Almendros

Summary: This research has achieved a selective palladium-catalyzed reaction sequence, leading to the synthesis of novel 2-iodo-1-aryl-9H-carbazoles. The observed formation of 2-iodocarbazoles in contrast to gold catalysis suggests a metal-controlled cyclization through chemo- and regioselective alkyl migration and iodonium migration.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Observing Single-Atom Catalytic Sites During Reactions with Electrospray Ionization Mass Spectrometry

Max J. Hulsey, Geng Sun, Philippe Sautet, Ning Yan

Summary: The article discusses the use of electrospray ionization mass spectrometry (ESI-MS) to study single-atom catalysts supported on polyoxometalates in catalytic reactions, revealing the composition of active sites and their evolution in the catalytic cycle.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Borane/Gold(I)-Catalyzed C-H Functionalization Reactions and Cycloaddition Reactions of Amines and α-Alkynylenones

Jun-Jie Tian, Wei Sun, Rui-Rui Li, Gui-Xiu Tian, Xiao-Chen Wang

Summary: A borane/gold(I) co-catalytic system was designed and applied in C-H functionalization reactions and cycloaddition reactions between tertiary amines and alpha-alkynylenones, efficiently introducing a furan ring into the amine molecule.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Branched Tertiary Amines from Aldehydes and α-Olefins by Combined Multiphase Tandem Reactions

Marc Strohmann, Andreas J. Vorholt, Walter Leitner

Summary: This study presents a method for transforming olefins into branched amines by combining hydroformylation/aldol condensation tandem reaction with reductive amination. The method utilizes a combined multiphase system that can be recycled 9 times. The study demonstrates the feasibility of the method and its potential applications in the production of surfactants.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Electrochemical cascade reactions: an account of recent developments for this modern strategic tool in the arsenal of chemical synthesis

Manoj Kumar Yadav, Sushobhan Chowdhury

Summary: In order to meet the growing demand for synthetic molecules or materials, the field of organic synthesis needs to be more efficient in producing molecules in a shorter time. This can be achieved through green chemical synthesis, which involves reducing the use of solvents, catalysts, reagents, time, effort, and waste. Integrated organic synthesis, particularly through electrochemical cascade reactions, is a strategic tool for fulfilling demand while maintaining green parameters.

GREEN CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Spirocyclic Compounds by a Ring-Expansion/Cationic Cyclization Cascade Reaction of Chlorosulfate Derivatives

Lara Cala, Ruben Rubio-Presa, Olaya Garcia-Pedrero, Francisco J. Fananas, Felix Rodriguez

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Applied

Scalable Synthesis of Esp and Rhodium(II) Carboxylates from Acetylacetone and RhCl3•xH2O

Elisa Martinez-Castro, Samuel Suarez-Pantiga, Abraham Mendoza

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Computational and Experimental Study of Turbo-Organomagnesium Amide Reagents: Cubane Aggregates as Reactive Intermediates in Pummerer Coupling

Ferran Planas, Stefanie V. Kohlhepp, Genping Huang, Abraham Mendoza, Fahmi Himo

Summary: The dynamic equilibria of organomagnesium reagents are studied using DFT calculations and kinetic experiments to investigate the Pummerer coupling between sulfoxides and turbo-organomagnesium amides. Heterometallic open cubane structures are shown to play a key role as reactive intermediates in turbo-organomagnesium amide mixtures through a concerted anion-anion coupling/S-O cleavage step. This research introduces a new reaction pathway and sheds light on the importance of open cubane organometallics in these mixtures.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

添加到收藏夹

Article Chemistry, Organic

Dihalogenation of Alkenes Using Combinations of N-Halosuccinimides and Alkali Metal Halides

Ruben Rubio-Presa, Olaya Garcia-Pedrero, Pablo Lopez-Matanza, Pablo Barrio, Felix Rodriguez

Summary: This method for vicinal dihalogenation of alkenes is simple, efficient, and eco-friendly, utilizing environmentally benign solvents and avoiding purification steps. Pure products are typically obtained through a simple aqueous workup.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Physical

Combined Experimental and Computational Study of Ruthenium N-Hydroxyphthalimidoyl Carbenes in Alkene Cyclopropanation Reactions

Ferran Planas, Matteo Costantini, Marc Montesinos-Magraner, Fahmi Himo, Abraham Mendoza

Summary: The study found that the slower dimerization reaction of NHPI-DA catalysis led to better selectivity; calculations showed multiple reaction pathways for the cyclopropanation of NHPI-DA, with carbene insertion being a key step; the stereoselectivity of the reaction depends on the intricate balance between various mechanistic scenarios.

ACS CATALYSIS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

Cationic cyclization reactions with alkyne terminating groups: a useful tool in biomimetic synthesis

Olaya Garcia-Pedrero, Felix Rodriguez

Summary: Cyclization reactions using cationic intermediates with alkynes as terminating groups offer wide synthetic possibilities, serving as precursors for different functionalities. This type of process shows potential, particularly in the biomimetic synthesis of natural products.

CHEMICAL COMMUNICATIONS (2022)

添加到收藏夹

Editorial Material Chemistry, Multidisciplinary

Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides

Kilian Colas, A. Catarina V. D. dos Santos, Stefanie Kohlhepp, Abraham Mendoza

Summary: In this study, the researchers enhanced the nucleophilicity and selectivity of Grignard reagents by introducing a bulky magnesium anilide additive, resulting in the direct synthesis of ketones from carboxylic acids.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides

Kilian Colas, A. Catarina V. D. dos Santos, Stefanie Kohlhepp, Abraham Mendoza

Summary: The addition of organometallic reagents to aliphatic carboxylic acids for the synthesis of ketones is limited to organolithium reagents, but can be extended to Grignard reagents using a bulky aniline-derived turbo-Hauser base. This method allows for the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

添加到收藏夹

Article Chemistry, Physical

Modular Enantioselective Synthesis of cis-Cyclopropanes through Self-Sensitized Stereoselective Photodecarboxylation with Benzothiazolines

Matteo Costantini, Abraham Mendoza

Summary: A modular approach from olefin materials to the synthesis of chiral cis-cyclopropanes is enabled by the discovery of the electron donor-acceptor interaction between 2-substituted benzothiazolines and N-hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, with benzothiazoline reagent serving as a photoreductant, stereoselective hydrogen-atom donor, and a Bronsted acid. This study introduces benzothiazolines as accessible and easily tunable self-sensitized photoreductants, expanding their potential applications beyond enantioselective synthesis of cis-cyclopropanes.

ACS CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Organic

Gold(I) Catalysis Applied to the Stereoselective Synthesis of Indeno[2,1-b]thiochromene Derivatives and Seleno Analogues

Cintia Virumbrales, Mahmoud A. E. A. A. A. El-Remaily, Samuel Suarez-Pantiga, Manuel A. Fernandez-Rodriguez, Felix Rodriguez, Roberto Sanz

Summary: This study describes a gold(I)-catalyzed cascade reaction for the stereoselective synthesis of sulfur- or selenium-containing indeno[1,2-b]chromene derivatives, involving a double cyclization process to form polycyclic structures by a proposed key gold-cyclopropyl carbene intermediate.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Modular Synthesis of (Borylmethyl)silanes through Orthogonal Functionalization of a Carbon Atom

Rajdip Chowdhury, Gabor Zoltan Elek, Beatriz Meana-Baamonde, Abraham Mendoza

Summary: (Borylmethyl)trimethylsilanes are important building blocks with unique reactivity in organic synthesis. However, the synthesis of more advanced derivatives is limited due to the requirement of advanced silicon intermediates. This study develops a one-pot synthesis of (borylmethyl)silanes using available alkyl, aryl, alkoxy, aryloxy, and silyl-hydrosilane materials. The reactivity of N-hydroxyphthalimidyl diazoacetate (NHPI-DA) in Si-H insertion and alpha-silyl redox-active esters in different decarboxylative borylation reactions is investigated.

ORGANIC LETTERS (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

N-Hydroxyphthalimidyl diazoacetate (NHPI-DA): a modular methylene linchpin for the C-H alkylation of indoles

Rajdip Chowdhury, Abraham Mendoza

Summary: This study investigates the use of redox-active carbenes in the expedited and divergent synthesis of functionalized indoles, showing high efficiency and selectivity with NHPI-DA. The method allows for swift elaboration of insertion products into boron and carbon substituents.

CHEMICAL COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light

Rajdip Chowdhury, Zhunzhun Yu, My Linh Tong, Stefanie Kohlhepp, Xiang Yin, Abraham Mendoza

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Generation of alkoxysulfonyl radicals from chlorosulfates and their intramolecular capture with alkynes to obtain sultones

Lara Cala, Olaya Garcia-Pedrero, Ruben Rubio-Presa, Francisco J. Fananas, Felix Rodriguez

CHEMICAL COMMUNICATIONS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Multicomponent and multicatalytic asymmetric synthesis of furo[2,3-b]pyrrole derivatives: further insights into the mode of action of chiral phosphoric acid catalysts

Lara Cala, Pedro Villar, Angel R. de Lera, Francisco J. Fananas, Rosana Alvarez, Felix Rodriguez

CHEMICAL SCIENCE (2020)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.