4.8 Article

Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)-Boron Lewis Acid Catalysis

Related references

Note: Only part of the references are listed.
Review Chemistry, Multidisciplinary

Advances in Electrochemical Decarboxylative Transformation Reactions

Velayudham Ramadoss et al.

Summary: Carboxylic acids are considered environmentally benign alternatives in various organic transformations due to their non-toxic, stable, and inexpensive properties. Electrochemical decarboxylation has emerged as an efficient methodology for carbon-carbon or carbon-heteroatom bond formations, providing a green and sustainable protocol without the need for chemical oxidants and strong bases. This method also shows good tolerance with various functional groups.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Review Chemistry, Multidisciplinary

Strategies for the Photocatalytic Generation of Carbanion Equivalents for Reductant-Free C-C Bond Formations

Karsten Donabauer et al.

Summary: This article discusses the application of photocatalysis in organic chemistry since the beginning of the 21st century, as well as the latest research on expanding photocatalysis into the realm of polar ionic reactions. Special attention is paid to the photocatalytic formation of anionic carbon nucleophiles for the formation of C-C bonds, avoiding the drawbacks of traditional organometallic reactions that require the use of a large amount of reducing metal.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

Review Chemistry, Applied

Decarboxylation-Initiated Intermolecular Carbon-Heteroatom Bond Formation

Zhongyi Zeng et al.

Summary: Carboxylic acids and their derivatives play a key role in decarboxylative couplings for constructing C-C and C-heteroatom bonds, offering a complementary bond disconnection to traditional cross-coupling methods. By undergoing decarboxylation and reacting with other heteroatom electrophiles and nucleophiles, these compounds replace carboxylate groups with valuable and prevalent heteroatom functionalities.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Stephanie G. E. Amos et al.

Summary: In this study, aryl-substituted ethynylbenziodoxolone reagents were found to be directly activated by visible light irradiation, acting as oxidants and radical traps in various EBX-mediated processes. This eliminates the need for a photocatalyst, simplifying the reaction conditions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Photoredox-Catalyzed Benzylic Esterification via Radical-Polar Crossover

Bumpei Maeda et al.

Summary: This article presents photoredox-catalyzed C-O bond formation reactions, enabling the diverse transformation of pharmaceuticals through decarboxylative esterification and C-H bond conversion.

ORGANIC LETTERS (2021)

Article Chemistry, Physical

A Platform for Decarboxylative Couplings via Photoredox Catalysis: Direct Access to Carbocations from Carboxylic Acids for Carbon-Oxygen Bond Formation

Peijun Li et al.

Summary: This study demonstrates a novel method for constructing carbon-oxygen bonds using a dual photoredox/iodine(III) platform directly from simple carboxylic acids and alcohols. By utilizing a radical-polar crossover event to generate a carbocation intermediate, this activation platform overcomes the electronically mismatched nature inherent in previous radical-based decarboxylative couplings, enabling a broad application across different types of carboxylic acid substrates.

ACS CATALYSIS (2021)

Review Chemistry, Organic

Recent advances of Ritter reaction and its synthetic applications

Meng-En Chen et al.

Summary: This review article comprehensively surveys Ritter reactions from 2014 to 2020, discussing various types of reactions and their synthetic applications, including oxidative Ritter-type reactions, tandem Ritter reactions, and asymmetric Ritter reactions. It also systematically summarizes the application of Ritter reactions in total synthesis of natural products, as well as in the preparation of drugs, bioactive compounds, and functional molecules.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Organic

Reactions promoted by hypervalent iodine reagents and boron Lewis acids

Ayan Dasgupta et al.

Summary: Understanding the role of boranes in hypervalent iodine chemistry can lead to new reactivities for organic synthesis. Boranes have shown to be viable alternatives for transformations typically dominated by transition metals, with the potential to mitigate some drawbacks of metal systems. Efforts to harness the diverse potential of boranes in hypervalent iodine chemistry can uncover exciting reactivity applicable across various disciplines, including pharmaceutical sciences.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

A Direct S0→Tn Transition in the Photoreaction of Heavy-Atom-Containing Molecules

Masaya Nakajima et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Organophotoredox-Catalyzed Decarboxylative C(sp3)-O Bond Formation

Shotaro Shibutani et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

When Light Meets Nitrogen-Centered Radicals: From Reagents to Catalysts

Xiao-Ye Yu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Multidisciplinary

Iodine Catalysis for C(sp3)-H Fluorination with a Nucleophilic Fluorine Source

Daniel Bafaluy et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

Eric W. Webb et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Fluorohydration of alkynes via I(I)/I(III) catalysis

Jessica Neufeld et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Organic

Electrochemical Decarboxylative N-Alkylation of Heterocycles

Tao Sheng et al.

ORGANIC LETTERS (2020)

Review Chemistry, Multidisciplinary

Catalytic reductive aminations using molecular hydrogen for synthesis of different kinds of amines

Kathiravan Murugesan et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Intermolecular Radical C(sp3)-H Amination under Iodine Catalysis

Alexandra E. Bosnidou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Applied

Photocatalytic Oxidative Iodination of Electron-Rich Arenes

Rok Narobe et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Article Chemistry, Multidisciplinary

Alkyliodines in High Oxidation State: Enhanced Synthetic Possibilities and Accelerated Catalyst Turn-Over

Alexandra E. Bosnidou et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Multidisciplinary Sciences

Hindered dialkyl ether synthesis with electrogenerated carbocations

Jinbao Xiang et al.

NATURE (2019)

Review Chemistry, Multidisciplinary

Reductive radical-polar crossover: traditional electrophiles in modern radical reactions

Lena Pitzer et al.

CHEMICAL SCIENCE (2019)

Article Chemistry, Multidisciplinary

Photocatalytic carbanion generation - benzylation of aliphatic aldehydes to secondary alcohols

Karsten Donabauer et al.

CHEMICAL SCIENCE (2019)

Article Chemistry, Organic

Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers

Kensuke Kiyokawa et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2018)

Review Chemistry, Multidisciplinary

Hypervalent Iodine Reagents by Anodic Oxidation: A Powerful Green Synthesis

Mohamed Elsherbini et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Review Chemistry, Multidisciplinary

Decarboxylative reactions with and without light - a comparison

Johanna Schwarz et al.

GREEN CHEMISTRY (2018)

Review Chemistry, Organic

Recent Progress on Radical Decarboxylative Alkylation for Csp3-C Bond Formation

Yajun Li et al.

SYNTHESIS-STUTTGART (2017)

Review Chemistry, Multidisciplinary

Iodine(III) Reagents in Radical Chemistry

Xi Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Article Chemistry, Multidisciplinary

Catalytic Friedel-Crafts Reactions of Highly Electronically Deactivated Benzylic Alcohols

Vuk D. Vukovic et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

C-C Coupling of Benzyl Fluorides Catalyzed by an Electrophilic Phosphonium Cation

Jiangtao Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Ritter-type amination of C-H bonds at tertiary carbon centers using iodic acid as an oxidant

Kensuke Kiyokawa et al.

CHEMICAL COMMUNICATIONS (2016)

Review Chemistry, Multidisciplinary

Biobased Amines: From Synthesis to Polymers; Present and Future

Vincent Froidevaux et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Indranirekha Saikia et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Hypervalent iodine(III) fluorinations of alkenes and diazo compounds: new opportunities in fluorination chemistry

Stefanie V. Kohlhepp et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Chemistry, Multidisciplinary

Advances in Iodine(III)-Mediated Halogenations: A Versatile Tool to Explore New Reactivities and Selectivities

Andreas M. Arnold et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Multidisciplinary

Acid Activation in Phenyliodine Dicarboxylates: Direct Observation, Structures, and Implications

Susana Izquierdo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Chemistry, Multidisciplinary

Contemporary Carbocation Chemistry: Applications in Organic Synthesis

Rajasekhar Reddy Naredla et al.

CHEMICAL REVIEWS (2013)

Review Chemistry, Organic

Ritter Reaction: Recent Catalytic Developments

Amandine Guerinot et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

Article Chemistry, Medicinal

The Medicinal Chemist's Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates

Stephen D. Roughley et al.

JOURNAL OF MEDICINAL CHEMISTRY (2011)

Review Chemistry, Multidisciplinary

Diaryliodonium Salts: A Journey from Obscurity to Fame

Eleanor A. Merritt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Review Chemistry, Multidisciplinary

Chemistry of Polyvalent Iodine

Viktor V. Zhdankin et al.

CHEMICAL REVIEWS (2008)

Review Chemistry, Multidisciplinary

Hypervalent iodine chemistry in synthesis: Scope and new directions

T Wirth

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Article Chemistry, Organic

Progressive direct iodination of sterically hindered alkyl substituted benzenes

S Stavber et al.

SYNTHESIS-STUTTGART (2002)