☆ 4.8 Article

Decarboxylative Amidation of Aryl/Heteroarylacetic Acids via Activated Esters through Traceless α-Functionalized Benzylic Radicals

ORGANIC LETTERS (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

Decarboxylative cross-nucleophile coupling via ligand-to-metal charge transfer photoexcitation of Cu(II) carboxylates

Qi Yukki Li et al.

Summary: Reactions that allow for the formation of carbon-nitrogen, carbon-oxygen, and carbon-carbon bonds are crucial in synthetic chemistry. This study presents a copper-mediated, net-oxidative decarboxylative coupling reaction under visible-light irradiation, which enables the conversion of substrates without requiring harsh reaction conditions.

NATURE CHEMISTRY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis

Pin Xu et al.

Summary: The first enantioselective radical trifluoromethylation of benzylic C-H bonds has been achieved using a cooperative photoredox and copper catalysis system. This method provides straightforward access to structurally diverse benzylic trifluoromethylation products with excellent enantioselectivities under mild conditions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Article Chemistry, Organic

Visible-Light-Catalyzed Radical-Radical Cross-Coupling Reaction of Benzyl Trifluoroborates and Carbonyl Compounds to Sterically Hindered Alcohols

Hao-Luo Jiang et al.

Summary: An organic dye catalyzed direct radical-radical cross-coupling reaction, powered by visible light and not requiring any external oxidants or reductants, is reported here. In this reaction, benzyl trifluoroborates are oxidized by excited-state 4Cz-IPN to generate benzyl radicals, and the resulting boron trifluoride acts as a Lewis acid to reduce the reduction potential of carbonyl compounds. The dual roles of benzyl trifluoroborates enable the generation of various sterically hindered alcohols from aldehydes, ketones, diketones, and ketone esters.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Organic

Photoinduced Synthesis of Thiocyanates through Hydrogen Atom Transfer and One-Pot Derivatization to Isothiocyanates

Bumpei Maeda et al.

Summary: This article describes a photoinduced benzylic C-H thiocyanation method. A series of alkyl thiocyanates were efficiently synthesized using Selectfluor as the oxidant, and one-pot isothiocyanation was achieved following the C-H thiocyanation. The resulting thiocyanates and isothiocyanates can be applied to the divergent transformation of pharmaceuticals.

ORGANIC LETTERS (2022)

Add to Collection

Article Chemistry, Physical

Copper-Catalyzed C(sp3)-H Methylation via Radical Relay

Bryan C. Figula et al.

Summary: In this study, a radical relay C-H methylation method using a beta-diketiminate copper catalyst was developed, enabling the methylation of unactivated C(sp(3))-H bonds. By utilizing the bench-stable DABAL-Me-3 as a reagent, methylation of various substrates with both activated and unactivated C(sp(3))-H bonds was achieved with minimal overmethylation. Mechanistic studies suggested the involvement of a copper(II) methyl intermediate that reacts with methyl radicals and radicals R-center dot to form R-Me bonds.

ACS CATALYSIS (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis

Pin Xu et al.

Summary: The first enantioselective radical trifluoromethylation of benzylic C-H bonds has been established by a cooperative photoredox and copper catalysis system, providing straightforward access to structurally diverse benzylic trifluoromethylation products in good yields with excellent enantioselectivities under mild conditions. Merging the cooperative photoredox catalysis with copper catalysis is essential for the reaction, where the photoredox catalysis is used for the generation of benzylic radicals from alkyl arenes through a hydrogen atom transfer process and the copper catalysis is used for the enantioselective trifluoromethylation of the benzylic radicals.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Add to Collection

Review Chemistry, Multidisciplinary

Decarboxylative Halogenation of Organic Compounds

Andrii Varenikov et al.

Summary: Decarboxylative halogenation is a crucial method for synthesizing organic halides by converting carboxylic acids to the corresponding organic halides. This method involves the synthesis of organic iodides, bromides, chlorides, and fluorides, providing a wide range of methods and advantages.

CHEMICAL REVIEWS (2021)

Add to Collection

Article Chemistry, Organic

tert-Butyl Nitrite as a Twofold Hydrogen Abstractor for Dehydrogenative Coupling of Aldehydes with N-Hydroxyimides

Peng-Fei Dai et al.

Summary: A synthetically practical transition metal/catalyst/halogen-free dehydrogenative coupling of aldehydes with N-hydroxyimides solely promoted by tert-butyl nitrite under mild conditions was developed. A diverse array of N-hydroxyimide esters can be prepared from either aliphatic or aromatic aldehydes, with benzoyl-substituted aldehydes also being suitable.

ORGANIC LETTERS (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Acyclic Twisted Amides

Guangrong Meng et al.

Summary: This contribution provides a comprehensive overview of acyclic twisted amides since 1993, focusing on their key structural properties and applications in various fields of chemistry.

CHEMICAL REVIEWS (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Radical philicity and its role in selective organic transformations

Faeze Parsaee et al.

Summary: Radical philicity, the ability of radicals to act as nucleophiles or electrophiles, is an important concept in organic chemistry. Traditionally, radicals are considered electron deficient, but the term "electron deficient" can imply electrophilicity in modern literature. This discrepancy has led to misconceptions about radical behavior, as many radicals actually exhibit nucleophilic behavior. This review aims to guide the understanding and prediction of radical philicity, demonstrating that not all radicals behave as electrophiles.

NATURE REVIEWS CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation

Joydev K. Laha et al.

Summary: An improved gram-scale synthesis of sildenafil has been developed using arylacetic acid, a cheap oxidant, and water, reducing costs by half and showing broad application in the synthesis of related derivatives.

NEW JOURNAL OF CHEMISTRY (2021)

Add to Collection

Review Chemistry, Organic

Arylacetic Acids in Organic Synthesis

Chenxi Yang et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Organic

Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions

Joydev K. Laha et al.

ORGANIC LETTERS (2020)

Add to Collection

Review Chemistry, Organic

Non-Classical Amide Bond Formation: Transamidation and Amidation of Activated Amides and Esters by Selective N-C/O-C Cleavage

Guangchen Li et al.

SYNTHESIS-STUTTGART (2020)

Add to Collection

Review Chemistry, Organic

One-Electron Reduction of Redox-Active Esters to Generate Carbon-Centered Radicals

Pengfei Niu et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Cleavage of C(aryl)-CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions

Peng-Fei Dai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection

Review Chemistry, Multidisciplinary

tert-Butyl Nitrite (TBN), a Multitasking Reagent in Organic Synthesis

Anjali Dahiya et al.

CHEMISTRY-AN ASIAN JOURNAL (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators

Alastair J. J. Lennox et al.

CHEMICAL SCIENCE (2018)

Add to Collection

Review Chemistry, Applied

N-(Acyloxy)phthalimides as Redox-Active Esters in Cross-Coupling Reactions

Sandip Murarka

ADVANCED SYNTHESIS & CATALYSIS (2018)

Add to Collection

Article Chemistry, Organic

Low-Valent Titanium-Mediated Radical Conjugate Addition Using Benzyl Alcohols as Benzyl Radical Sources

Takuya Suga et al.

ORGANIC LETTERS (2018)

Add to Collection

Article Chemistry, Organic

Impact of Conjugation and Hyperconjugation on the Radical Stability of Allylic and Benzylic Systems: A Theoretical Study

Daniel J. Van Hoomissen et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Add to Collection

Article Chemistry, Organic

Oxidative decarboxylation of arylacetic acids in water: One-pot transition-metal-free synthesis of aldehydes and ketones

Trimbak B. Mete et al.

TETRAHEDRON LETTERS (2017)

Add to Collection

Article Chemistry, Physical

A Cross-Coupling Approach to Amide Bond Formation from Esters

Taoufik Ben Halima et al.

ACS CATALYSIS (2017)

Add to Collection

Review Chemistry, Multidisciplinary

Recent Advances in Radical C-H Activation/Radical Cross-Coupling

Hong Yi et al.

CHEMICAL REVIEWS (2017)

Add to Collection

Review Chemistry, Multidisciplinary

Decarboxylation as the Key Step in C-C Bond-Forming Reactions

Tuhin Patra et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Add to Collection

Review Chemistry, Multidisciplinary

Nonclassical Routes for Amide Bond Formation

Renata Marcia de Figueiredo et al.

CHEMICAL REVIEWS (2016)

Add to Collection

Article Chemistry, Organic

General Method for the Preparation of Active Esters by Palladium-Catalyzed Alkoxycarbonylation of Aryl Bromides

Angelina M. de Almeida et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Add to Collection

Review Chemistry, Multidisciplinary

Catalytic amide formation from non-activated carboxylic acids and amines

Helena Lundberg et al.

CHEMICAL SOCIETY REVIEWS (2014)

Add to Collection

Article Chemistry, Organic

Aldehydes and Ketones Formation: Copper-Catalyzed Aerobic Oxidative Decarboxylation of Phenylacetic Acids and α-Hydroxyphenylacetic Acids

Qiang Feng et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Organocatalytic Amidation and Esterification of Aldehydes with Activating Reagents by a Cross-Coupling Strategy

Bin Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Add to Collection

Review Neurosciences

Moclobemide: Therapeutic use and clinical studies

U Bonnet

CNS DRUG REVIEWS (2003)

Add to Collection

© Peeref 2019-2024. All rights reserved.