☆ 4.8 Article

Coupling of α-bromoamides and unactivated alkenes to form γ-lactams through EDA and photocatalysis

CHEMICAL SCIENCE (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

Photochemical Organocatalytic Benzylation of Allylic C-H Bonds

Emilien Le Saux et al.

Summary: We report a radical-based organocatalytic method for the direct benzylation of allylic C-H bonds. This method uses nonfunctionalized allylic substrates and readily available benzyl radical precursors, and is driven by visible light. By controlling two orthogonal radical generation paths, it enables the selective coupling of allylic and benzylic radicals, thus expanding the synthetic potential of organic chemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Review Chemistry, Multidisciplinary

Enantioselective Photochemical Reactions Enabled by Triplet Energy Transfer

Johannes Grosskopf et al.

Summary: This review provides a comprehensive survey on enantioselective photochemical reactions achieved through triplet sensitization. It is shown that highly selective enantioselective photochemical reactions can be achieved by using appropriate chiral sensitizers or a dual catalytic approach.

CHEMICAL REVIEWS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Sustainable Thioetherification via Electron Donor-Acceptor Photoactivation Using Thianthrenium Salts

Maria Jesus Cabrera-Afonso et al.

Summary: This study developed a photoinduced, open-to-air C-H thioetherification method using readily available reagents, which tolerates various functional groups. The intact C(sp(2))-halogen bonds allow late-stage installation of sulfide motif and further modification with traditional C-X bond cleavage methods. Mechanistic investigations support the proposed electron donor-acceptor complex scenario.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Tetrachlorophthalimides as Organocatalytic Acceptors for Electron Donor-Acceptor Complex Photoactivation

Wei Zhou et al.

Summary: In this study, it was found that tetrachlorophthalimides can act as effective organocatalytic acceptors, triggering radical reactions not amenable to previous catalytic methods. This finding allowed the development of mechanistically distinct radical reactions and the evaluation of catalytic cycle via quantum yield measurements.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Strain-Release [2π+2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer

Renyu Guo et al.

Summary: Saturated bicycles are increasingly important in the design and development of new pharmaceuticals. This article describes a new strategy for synthesizing bicyclo[2.1.1]hexanes, which have defined exit vectors but are underexplored as building blocks in terms of substitution patterns. The process involves sensitization of a bicyclo[1.1.0]butane followed by cycloaddition with an alkene. The scope and mechanistic details of the method are discussed.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Physical

A Pyridine-Based Donor-Acceptor Molecule: A Highly Reactive Organophotocatalyst That Enables the Reductive Cleavage of C-Br Bonds through Halogen Bonding

Natsuki Kato et al.

Summary: We report a novel pyridine-based photoredox catalyst that enables the direct photocatalytic reductive cleavage of C-Br bond in alkyl bromides to generate radicals. The catalyst allows for the C-C coupling reaction of alkyl bromides, including unactivated ones, under ambient conditions without additional activating agents, resulting in good yields.

ACS CATALYSIS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Photoredox Activation of Anhydrides for the Solvent-Controlled Switchable Synthesis of gem-Difluoro Compounds

Rahul Giri et al.

Summary: In this study, a simple, mild, and switchable protocol was developed to access various gem-difluoro compounds using chlorodifluoroacetic anhydride as a versatile and cost-effective reagent. The mechanism of the reaction was also investigated, demonstrating the advantages of this method in terms of product selectivity and reaction applicability.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Photochemical C-F Activation Enables Defluorinative Alkylation of Trifluoroacetates and -Acetamides

Mark W. Campbell et al.

Summary: A photochemically mediated method has been successfully developed for the defluorinative alkylation of ethyl trifluoroacetate, providing an efficient pathway for the synthesis of novel gem-difluoro analogs. This method can also be used for the hydroalkylation of a diverse suite of alkenes, expanding the range of substrates for the reaction.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes

Eduardo de Pedro Beato et al.

Summary: The study introduces a modular class of organic catalysts that can form photoactive electron donor-acceptor complexes with radical precursors. Excitation with visible light generates open-shell intermediates, allowing for the development of mechanistically distinct radical reactions encompassing redox-neutral and net-reductive processes. The organic catalysts demonstrate the ability to turn over and iteratively drive every catalytic cycle, enabling direct radical functionalization and enantioselective radical catalysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes

Giacomo E. M. Crisenza et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection

Review Chemistry, Multidisciplinary

Triplet Energy Transfer Photocatalysis: Unlocking the Next Level

Felix Strieth-Kalthoff et al.

CHEM (2020)

Add to Collection

Article Chemistry, Organic

In Situ-Generated Halogen-Bonding Complex Enables Atom Transfer Radical Addition (ATRA) Reactions of Olefins

Kazuki Matsuo et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

Sungwoo Jung et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection

Review Chemistry, Multidisciplinary

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

Quan-Quan Zhou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer

Mary Elisabeth Daub et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Add to Collection

Article Chemistry, Physical

3-Acetoxyquinuclidine as Catalyst in Electron Donor-Acceptor Complex-Mediated Reactions Triggered by Visible Light

Irene Bosque et al.

ACS CATALYSIS (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Jingjing Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Review Chemistry, Multidisciplinary

Energy transfer catalysis mediated by visible light: principles, applications, directions

Felix Strieth-Kalthoff et al.

CHEMICAL SOCIETY REVIEWS (2018)

Add to Collection

Review Chemistry, Organic

Electron Donor-Acceptor Complexes in Perfluoroalkylation Reactions

Al Postigo

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Photoinduced Deaminative Borylation of Alkylamines

Jingjing Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Add to Collection

Article Chemistry, Physical

Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate To Generate Trifluoromethyl Thioethers

Jian He et al.

ACS CATALYSIS (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Evidence for Triplet Sensitization in the Visible-Light-Induced [2+2] Photocycloaddition of Eniminium Ions

Fabian M. Hoermann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Add to Collection

Article Chemistry, Physical

Visible-Light-Promoted Atom Transfer Radical Cyclization of Unactivated Alkyl Iodides

Yangyang Shen et al.

ACS CATALYSIS (2017)

Add to Collection

Article Chemistry, Organic

Photoredox Catalyzed Intramolecular Fluoroalkylarylation of Unactivated Alkenes

Zuxiao Zhang et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Add to Collection

Article Chemistry, Multidisciplinary

β-Selective Reductive Coupling of Alkenylpyridines with Aldehydes and Imines via Synergistic Lewis Acid/Photoredox Catalysis

Katarzyna N. Lee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Add to Collection

Article Chemistry, Multidisciplinary

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

Mattia Silvi et al.

NATURE CHEMISTRY (2017)

Add to Collection

Article Multidisciplinary Sciences

Photoinduced decarboxylative borylation of carboxylic acids

Alexander Fawcett et al.

SCIENCE (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Donor-Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)-C(sp3) Cleavage and Allylation/Alkenylation

Jing Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Article Chemistry, Applied

Copper-Catalyzed Aminodifluoroalkylation of Alkenes with -Bromodifluoroacetamides: Synthesis of 3,3-Difluoropyrrolidin-2-ones

Yunhe Lv et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective Crossed Photocycloadditions of Styrenic Olefins by Lewis Acid Catalyzed Triplet Sensitization

Zachary D. Miller et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Review Chemistry, Multidisciplinary

Photochemical Stereocontrol Using Tandem Photoredox-Chiral Lewis Acid Catalysis

Tehshik P. Yoon

ACCOUNTS OF CHEMICAL RESEARCH (2016)

Add to Collection

Review Chemistry, Organic

Biologically active γ-lactams: synthesis and natural sources

J. Caruano et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Add to Collection

Article Chemistry, Organic

Cascade Photoredox/Iodide Catalysis: Access to Difluoro-γ-lactams via Aminodifluoroalkylation of Alkenes

Muliang Zhang et al.

ORGANIC LETTERS (2016)

Add to Collection

Article Multidisciplinary Sciences

Enantioselective photochemistry through Lewis acid-catalyzed triplet energy transfer

Travis R. Blum et al.

SCIENCE (2016)

Add to Collection

Article Chemistry, Physical

Different Behaviors of a Cu Catalyst in Amine Solvents: Controlling N and O Reactivities of Amide

Yu Yamane et al.

ACS CATALYSIS (2016)

Add to Collection

Review Chemistry, Physical

Organic Synthesis Enabled by Light-Irradiation of EDA Complexes: Theoretical Background and Synthetic Applications

Carolina G. S. Lima et al.

ACS CATALYSIS (2016)

Add to Collection

Article Chemistry, Physical

Thiyl-Radical-Catalyzed Photoreductive Hydrodifluoroacetamidation of Alkenes with Hantzsch Ester as a Multifunctional Reagent

Wenhao Huang et al.

ACS CATALYSIS (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Copper-Catalyzed 1,2-Addition of α-Carbonyl Iodides to Alkynes

Tao Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Add to Collection

Review Chemistry, Organic

Recent progress towards transition metal-catalyzed synthesis of γ-lactams

Long-Wu Ye et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes

Elena Arceo et al.

NATURE CHEMISTRY (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Merging visible-light photoredox and Lewis acid catalysis for the functionalization and arylation of glycine derivatives and peptides

Shaoqun Zhu et al.

CHEMICAL COMMUNICATIONS (2012)

Add to Collection

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Protonation of Nitronates Utilizing an Organocatalyst Chiral Only at Sulfur

Kyle L. Kimmel et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Add to Collection

Article Chemistry, Multidisciplinary

Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts

John D. Nguyen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Add to Collection

Article Chemistry, Multidisciplinary

Efficient Regio- and Stereoselective Formation of Azocan-2-ones via 8-Endo Cyclization of α-Carbamoyl Radicals

Xinqiang Fang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Add to Collection

Article Chemistry, Multidisciplinary

Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to γ-lactams

Dustin E. A. Raup et al.

NATURE CHEMISTRY (2010)

Add to Collection

Article Chemistry, Multidisciplinary

Amide Enolate Additions to Acylsilanes: In Situ Generation of Unusual and Stereoselective Homoenolate Equivalents

Robert B. Lettan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Add to Collection

Review Biochemistry & Molecular Biology

Chemistry and biology of non-tetramic gamma-hydroxy-gamma-lactams and gamma-alkylidene-gamma-lactams from natural sources

Bastien Nay et al.

NATURAL PRODUCT REPORTS (2009)

Add to Collection

Review Chemistry, Multidisciplinary

Atom transfer radical addition and polymerization reactions catalyzed by ppm amounts of copper complexes

Tomislav Pintauer et al.

CHEMICAL SOCIETY REVIEWS (2008)

Add to Collection

Article Chemistry, Organic

Stereoselective synthesis of highly substituted γ-lactams by the [3+2] annulation of α-siloxy allylic silanes with chlorosulfonyl isocyanate

A Romero et al.

ORGANIC LETTERS (2006)

Add to Collection

Article Chemistry, Physical

Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex

MS Lowry et al.

CHEMISTRY OF MATERIALS (2005)

Add to Collection

© Peeref 2019-2024. All rights reserved.