4.7 Article

Visible-light-mediated amidation from carboxylic acids and tertiary amines via C-N cleavage

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, Multidisciplinary

Decarboxylative Acylation of Carboxylic Acids: Reaction Investigation and Mechanistic Study

Xiaopeng Wu et al.

Summary: This study reports a novel ketone synthesis method using a photoredox-nickel catalyst to react common aliphatic acids with aromatic and aliphatic thioesters. It efficiently constructs structurally diverse ketones with high yields. The method demonstrates excellent selectivity and functional group compatibility, representing a significant advancement in ketone synthesis.

CCS CHEMISTRY (2022)

Article Multidisciplinary Sciences

Highly selective synthesis of all-carbon tetrasubstituted alkenes by deoxygenative alkenylation of carboxylic acids

Yantao Li et al.

Summary: The authors present a method to synthesize tetrasubstituted olefins via dual photo- and nickel catalysis under an air atmosphere, without the need for an inert atmosphere. The synthesis of these compounds under mild conditions is challenging, but the authors were able to achieve it by using readily available carboxylic acids and alkenyl triflates. The method shows promise for applications in complex molecule modification and gram-scale synthesis.

NATURE COMMUNICATIONS (2022)

Review Chemistry, Multidisciplinary

Visible Light-Driven Radical-Mediated C-C Bond Cleavage/Functionalization in Organic Synthesis

Xiao-Ye Yu et al.

Summary: In recent years, visible light photoredox-catalyzed radical-mediated C-C bond cleavage reactions have emerged as a powerful alternative method for overcoming the thermodynamic and kinetic barrier of C-C bond cleavage in diverse molecular scaffolds. These reactions provide an efficient way to construct structurally diverse molecular skeletons, contributing to the development in the field of synthetic organic chemistry.

CHEMICAL REVIEWS (2021)

Article Chemistry, Organic

Synthesis of Trifluoromethylated Dithiocarbamates via Photocatalyzed Substitution Reaction: Pentafluoropyridine as Activating Reagent

Artem A. Zemtsov et al.

Summary: The method involves nucleophilic trifluoromethylation, derivatization of the silyloxy group, and substitution of the fluorinated pyridinyloxy group, leading to the synthesis of trifluoromethyl-substituted dithiocarbamates.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Pd-Catalyzed Oxidative Aminocarbonylation of Arylboronic Acids with Unreactive Tertiary Amines via C-N Bond Activation

Yuvraj A. Kolekar et al.

Summary: An efficient method for synthesizing tertiary amides from aryl boronic acids and inert tertiary amines via oxidative carbonylation was presented, with significantly reduced homocoupling biarylketone formation. The use of homogeneous PdCl2/CuI and heterogeneous Pd/C catalysts promotes C(sp(3))-N bond activation between tertiary amines and aryl boronic acids, utilizing a ligand-free, base-free, and recyclable catalyst system with molecular oxygen as an ideal oxidant.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Visible-Light-Mediated Deoxyalkynylation of Activated Tertiary Alcohols

Muzi Li et al.

Summary: This paper describes a visible-light-induced deoxyalkynylation reaction of activated tertiary alcohols using ethynylbenziodoxole as the alkynylation reagent under mild reaction conditions. The desired C(sp(3))-C(sp) coupling was smoothly achieved with 4-CzIPN photocatalyst, furnishing valuable alkynylation products with quaternary carbon centers in yields ranging from 37% to 84%.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)

William D. G. Brittain et al.

Summary: This work utilizes pentafluoropyridine (PFP) in the deoxyfluorination of carboxylic acids to acyl fluorides and in a one-pot amide bond formation. The method allows for high yields of amides to be readily obtained under mild conditions.

ORGANIC LETTERS (2021)

Article Multidisciplinary Sciences

Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

Yunyun Ning et al.

Summary: The development of catalytic amide bond-forming methods is important as it has the potential to overcome the limitations of traditional methods using superstoichiometric activating reagents. This study demonstrates an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by FeI2, P(V)/P(III) and photoredox catalysis, avoiding the production of byproducts. This method allows for the smooth participation of a wide range of carboxylic acids in such reactions, generating structurally diverse amides in good yields.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Photoredox/nickel-catalyzed hydroacylation of ethylene with aromatic acids

Lili Zhang et al.

Summary: A novel hydroacylation reaction of ethylene with aromatic carboxylic acids using nickel and photoredox catalysis was reported, allowing for the conversion of feedstock chemicals into high-value products with moderate to good yields (up to 92%) in 2-6 hours under ambient conditions.

CHEMICAL COMMUNICATIONS (2021)

Article Multidisciplinary Sciences

Upgrading ketone synthesis direct from carboxylic acids and organohalides

Rehanguli Ruzi et al.

NATURE COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Ring-Closing Reaction via C-N Bond Metathesis for Rapid Construction of Saturated N-Heterocycles

Bangkui Yu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Catalytic Benzylation Reactions: From C–H Bond Activation to C–N Bond Activation

Tianxiao Jiang et al.

CHINESE JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Organic

Organocatalyzed Fluoride Metathesis

Daniel Mulryan et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Deoxygenative Deuteration of Carboxylic Acids with D2O

Muliang Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Multidisciplinary Sciences

A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes

Muliang Zhang et al.

NATURE COMMUNICATIONS (2018)

Article Multidisciplinary Sciences

Selective sp3 C-H alkylation via polarity-match-based cross-coupling

Chip Le et al.

NATURE (2017)

Article Chemistry, Multidisciplinary

Photoredox-Controlled Mono- and Di-Multifluoroarylation of C(sp3)-H Bonds with Aryl Fluorides

Jin Xie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Multicomponent Reactions with Cyclic Tertiary Amines Enabled by Facile C-N Bond Cleavage

Qiming Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Monofluoroalkenylation of Dimethylamino Compounds through Radical-Radical Cross-Coupling

Jin Xie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

Transition-metal catalysed C-N bond activation

Quanjun Wang et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Chemistry, Organic

Palladium-catalyzed hydroaminocarbonylation of alkenes with amines promoted by weak acid

Guoying Zhang et al.

TETRAHEDRON LETTERS (2016)

Article Chemistry, Multidisciplinary

Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides

Adam Noble et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2

Jie Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis

Daniel A. DiRocco et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

A novel Pd-catalyzed N-dealkylative carbonylation of tertiary amines for the preparation of amides

Tao Fang et al.

CHEMICAL COMMUNICATIONS (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 Multidisciplinary Sciences

Identifying mechanism-of-action targets for drugs and probes

Elisabet Gregori-Puigjane et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2012)

Article Chemistry, Multidisciplinary

Highly Efficient Amide Synthesis from Alcohols and Amines by Virtue of a Water-Soluble Gold/DNA Catalyst

Ye Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Review Multidisciplinary Sciences

Rethinking amide bond synthesis

Vijaya R. Pattabiraman et al.

NATURE (2011)

Article Chemistry, Organic

Aminocarbonylation of aryl halides using a nickel phosphite catalytic system

Jinhun Ju et al.

ORGANIC LETTERS (2007)