4.8 Article

Catalytic Oxidative Coupling of Phenols and Related Compounds

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

A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs)

Alina Dyadyuk et al.

Summary: A novel type of chiral redox disulfonate iron complex has been developed for asymmetric catalysis, effectively promoting the enantio-selective oxidative cross-coupling reaction between 2-naphthols and 2-aminonaphthalene derivatives, with high yields and exceptional enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Multidisciplinary Sciences

Biocatalytic oxidative cross-coupling reactions for biaryl bond formation

Lara E. Zetzsche et al.

Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.

NATURE (2022)

Article Chemistry, Organic

Novel Axially Chiral Ligand-Enabled Copper-Catalyzed Asymmetric Oxidative Coupling of 2-Naphthols for the Synthesis of 6,6′-Disubstituted BINOLs

Pengyang Wang et al.

Summary: Novel axially chiral ligands were designed and synthesized by merging chelating picolinic acid with substituted BINOLs. In-situ-prepared copper catalysts from the ligands and CuI enabled the asymmetric oxidative coupling of 2-naphthols, affording 6,6'-disubstituted BINOLs in up to 89% yield with good enantioselectivities (up to 96:4 e.r.).

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling

Xiao-Jing Zhao et al.

Summary: The challenging direct asymmetric catalytic aerobic oxidative cross-coupling of 2-naphthylamine and 2-naphthol using a novel Cu-I/SPDO system has been successfully developed for the first time, achieving high enantioselectivities and good yields. The DFT calculations suggest that specific interactions and stacking between the coupling partners play vital roles in the enantiocontrol of this reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes

Vlada Vershinin et al.

Summary: The study investigates the FeCl3-catalyzed oxidative cross-coupling reaction between phenols and aminonaphthalene derivatives, providing a sustainable alternative for preparing N,O-biaryl compounds. A catalytic cycle involving a ternary complex during the key oxidative coupling step is proposed based on a comprehensive kinetic investigation, and the reaction is shown to be regulated by off-cycle processes.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Tyrosine Derivatives with 3-Alkyloxindoles

Tomer Mintz et al.

Summary: This study reports a novel iron-catalyzed oxidative cross-coupling reaction between phenols and 3-alkyloxindole derivatives, leading to the synthesis of 3-alkyl-3-(hydroxyaryl)oxindole compounds with high selectivity. The generality of the conditions has been proven and can be applied to various substituted phenols, naphthols, and tyrosine derivatives. Additionally, modifications to the reaction conditions have enabled the conjugation of tyrosine-containing short peptides with oxindolylalanine (Oia) derivatives.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Electrochemistry

Get into flow: Design of experiments as a key technique in the optimization of anodic dehydrogenative C,C cross-coupling reaction of phenols in flow electrolyzers

Maximilian M. Hielscher et al.

Summary: This study presents a new strategy for optimizing electro-organic reactions using Design of Experiments (DoE), successfully increasing the yield of an example reaction to 85% and identifying various suitable reaction conditions through linear regression analysis.

ELECTROCHIMICA ACTA (2021)

Article Electrochemistry

Optimization Strategies for the Anodic Phenol-Arene Cross-Coupling Reaction

Maximilian Hielscher et al.

Summary: Dehydrogenative phenol-arene cross-coupling by direct anodic oxidation is a promising alternative to reductive cross-coupling, offering unusual regioselectivity via phenoxyl radicals. Optimization strategies were presented for two example reactions to improve space-time yield, particularly emphasizing the robustness of coupling reactions with syringol at high current densities. Classification of phenols and arenes using cyclic voltammetry allowed for the optimization of various clusters, leading to the synthesis and isolation of various biaryls with yields up to 85%.

CHEMELECTROCHEM (2021)

Article Chemistry, Multidisciplinary

Chiral Vanadium(V)-catalyzed Oxidative Coupling of 4-Hydroxycarbazoles

Ganesh T. Kamble et al.

Summary: Enantioselective oxidative couplings of 4-hydroxycarbazoles using a chiral dinuclear vanadium(V) complex have been achieved for the first time, with the corresponding dimeric 4-hydroxycarbazoles obtained in up to 90% ee under mild reaction conditions.

CHEMISTRY LETTERS (2021)

Review Chemistry, Organic

Oxidative dehydrogenative couplings of alkenyl phenols

William C. Neuhaus et al.

Summary: Nature utilizes alkenyl phenols in the construction of lignin, a key biopolymer, leading to the formation of various structures like lignans and neolignans through selective dimerization. Several methods have been developed to influence desired bond formations in these biologically relevant scaffolds, with the most biomimetic involving oxidative bond formation via dehydrogenative coupling. This review discusses progress in the synthesis of important molecules derived from alkenyl phenols, while also recognizing existing gaps and limitations in current research.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Organic

Chemo- and enantioselective hetero-coupling of hydroxycarbazoles catalyzed by a chiral vanadium(v) complex

Makoto Sako et al.

Summary: The catalytic enantioselective oxidative hetero-coupling of arenols using a chiral vanadium(V) complex allows for the efficient synthesis of axially chiral biarenols with high selectivity and wide functional group tolerance.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Multidisciplinary

Dehydrogenative Anodic C-C Coupling of Phenols Bearing Electron-Withdrawing Groups

Johannes L. Roeckl et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

A Decade of Electrochemical Dehydrogenative C,C-Coupling of Aryls

Johannes L. Roeckl et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Multidisciplinary

Synthesis of Biaryl-Bridged Cyclic Peptides via Catalytic Oxidative Cross-Coupling Reactions

Mor Ben-Lulu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Total Synthesis of Pyrolaside B: Phenol Trimerization through Sequenced Oxidative C-C and C-O Coupling

William C. Neuhaus et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Diastereoselective Synthesis of Benzoxanthenones

William C. Neuhaus et al.

CHEMISTRY-AN ASIAN JOURNAL (2020)

Article Chemistry, Organic

Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols

Hiroki Hayashi et al.

ORGANIC LETTERS (2020)

Article Chemistry, Physical

Regiodivergent Oxidative Cross-Coupling of Catechols with Persistent tert-Carbon Radicals

Masumi Sugawara et al.

ACS CATALYSIS (2020)

Article Chemistry, Organic

Copper Catalyzed Oxidative Arylation of Tertiary Carbon Centers

Prakash Basnet et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Total Syntheses of Herqulines B and C

Xu Zhu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Organic

Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling

Alexander Lipp et al.

ORGANIC LETTERS (2019)

Article Chemistry, Physical

Catalytic Aerobic Cross-Dehydrogenative Coupling of Phenols and Catechols

Wenbo Xu et al.

ACS CATALYSIS (2019)

Article Chemistry, Multidisciplinary

Synthesis of Highly Functionalized N,N-Diarylamides by an Anodic C,N-Coupling Reaction

Maurice Doerr et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Multidisciplinary

Oxidative Coupling of 3-Oxindoles with Indoles and Arenes

Houng Kang et al.

CHEMSUSCHEM (2019)

Article Chemistry, Multidisciplinary

Chromium-Salen Catalyzed Cross-Coupling of Phenols: Mechanism and Origin of the Selectivity

Yexenia Nieves-Quinones et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Organic

Total Synthesis of (S,S)-Tetramethylmagnolamine via Aerobic Desymmetrization

Zheng Huang et al.

ORGANIC LETTERS (2019)

Article Chemistry, Multidisciplinary

Selective Formation of 4,4′-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction

Benedikt Dahms et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Article Chemistry, Organic

Chiral Dinuclear Vanadium Complex-Mediated Oxidative Coupling of Resorcinols

Makoto Sako et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Selective Oxidative Phenol Coupling by Iron Catalysis

Hadas Shalit et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Concise Total Synthesis of Herqulines B and C

Chi He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Total Synthesis of Herquline B and C

Joshua B. Cox et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Physical

Phenol-Directed C-H Functionalization

Zheng Huang et al.

ACS CATALYSIS (2019)

Article Chemistry, Medicinal

Honokiol-Inspired Analogs as Inhibitors of Oral Bacteria

Amy E. Solinski et al.

ACS INFECTIOUS DISEASES (2018)

Article Chemistry, Multidisciplinary

A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine

Alexander Lipp et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Electrochemical Oxidative C-H Amination of Phenols: Access to Triarylamine Derivatives

Shan Tang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Medicinal

Asymmetric oxidative coupling of hydroxycarbazoles: Facile synthesis of (+)-bi-2-hydroxy-3-methylcarbazole

Makoto Sako et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2018)

Article Chemistry, Multidisciplinary

A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol

Takashi Yamamoto et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Organic

Stereoselective Synthesis of Optically Pure 2-Amino-2′-hydroxy-1,1′-binaphthyls

Hagit Forkosh et al.

ORGANIC LETTERS (2018)

Article Chemistry, Organic

Enantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights

Houng Kang et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Organic

Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid

A. Bochicchio et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

Review Chemistry, Multidisciplinary

Oxidative Cyclization in Natural Product Biosynthesis

Man-Cheng Tang et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Organic

Photocatalytic Phenol-Arene C-C and C-O Cross-Dehydrogenative Coupling

Anna Eisenhofer et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols

Hadas Shalit et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Organic

Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles

Houng Kang et al.

ORGANIC LETTERS (2017)

Article Multidisciplinary Sciences

External oxidant-free electrooxidative [3+2] annulation between phenol and indole derivatives

Kun Liu et al.

NATURE COMMUNICATIONS (2017)

Article Chemistry, Multidisciplinary

Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes

Anton Wiebe et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Synthesis of ortho-Azophenols by Formal Dehydrogenative Coupling of Phenols and Hydrazines or Hydrazides

Kenneth Virgel N. Esguerra et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

Short Syntheses of 4-Deoxycarbazomycin B, Sorazolon E, and (+)-Sorazolon E2

Makoto Sako et al.

CHEMISTRY-AN ASIAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

A Catalyst-Controlled Aerobic Coupling of ortho-Quinones and Phenols Applied to the Synthesis of Aryl Ethers

Zheng Huang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Organo-Iodine(III)-Catalyzed Oxidative Phenol-Arene and Phenol-Phenol Cross-Coupling Reaction

Koji Morimoto et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Organic

Facile and Selective Cross-Coupling of Phenols Using Selenium Dioxide

Thomas Quell et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Efficient Enantioselective Synthesis of Oxahelicenes Using Redox/Acid Cooperative Catalysts

Makoto Sako et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes

Sachin Narute et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

A novel type of catalysts for asymmetric oxidative coupling of 2-naphthol

V. A. Larionov et al.

RUSSIAN CHEMICAL BULLETIN (2016)

Article Chemistry, Multidisciplinary

Synthetic and Predictive Approach to Unsymmetrical Biphenols by Iron-Catalyzed Chelated Radical-Anion Oxidative Coupling

Anna Libman et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles

Lei Liu et al.

ORGANIC LETTERS (2015)

Review Chemistry, Organic

Adapting Melanogenesis to a Regioselective C-H Functionalization of Phenols

Kenneth Virgel N. Esguerra et al.

SYNLETT (2015)

Article Chemistry, Multidisciplinary

Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols

Bernd Elsler et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Photocatalytic Synthesis of Dihydrobenzofurans by Oxidative [3+2] Cycloaddition of Phenols

Travis R. Blum et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Selective Oxidative Homo- and Cross-Coupling of Phenols with Aerobic Catalysts

Young Eun Lee et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Controlling the Catalytic Aerobic Oxidation of Phenols

Kenneth Virgel N. Esguerra et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Efficient synthesis of neurotrophic honokiol using Suzuki-Miyaura reactions

Kenichi Harada et al.

TETRAHEDRON LETTERS (2014)

Article Chemistry, Organic

Concise total synthesis of honokiol via Kumada cross coupling

Jada Srinivas et al.

TETRAHEDRON LETTERS (2014)

Article Chemistry, Organic

Cobalt(II)-Porphyrin-Catalyzed Aerobic Oxidation: Oxidative Coupling of Phenols

Qing Jiang et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

Article Chemistry, Organic

Iron-Catalyzed Oxidative Cross-Coupling of Phenols and Alkenes

Umesh A. Kshirsagar et al.

ORGANIC LETTERS (2013)

Article Chemistry, Multidisciplinary

Efficient Anodic and Direct Phenol-Arene C,C Cross-Coupling: The Benign Role of Water or Methanol

Axel Kirste et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Organic

Ligand-Controlled Iron-Catalyzed Coupling of α-Substituted β-Ketoesters with Phenols

Regev Parnes et al.

ORGANIC LETTERS (2012)

Article Chemistry, Organic

Total Synthesis of Mycocyclosin

James R. Cochrane et al.

ORGANIC LETTERS (2012)

Article Chemistry, Multidisciplinary

Highly Selective Electrosynthesis of Biphenols on Graphite Electrodes in Fluorinated Media

Axel Kirste et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

Article Chemistry, Organic

OXIDATIVE COUPLING OF INDOLES WITH 3-OXINDOLES

Mikkel Jessing et al.

HETEROCYCLES (2011)

Article Chemistry, Organic

Anodic Coupling of Guaiacol Derivatives on Boron-Doped Diamond Electrodes

Axel Kirste et al.

ORGANIC LETTERS (2011)

Article Chemistry, Multidisciplinary

Anodic Phenol-Arene Cross-Coupling Reaction on Boron-Doped Diamond Electrodes

Axel Kirste et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Chemistry, Multidisciplinary

An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols

Benjamin Pickel et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Review Chemistry, Multidisciplinary

Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling

Marisa C. Kozlowski et al.

CHEMICAL SOCIETY REVIEWS (2009)

Article Chemistry, Multidisciplinary

Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols

Hiromichi Egami et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Iron-Catalyzed Tandem Oxidative Coupling and Annulation: An Efficient Approach to Construct Polysubstituted Benzofurans

Xingwei Guo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Multidisciplinary

Dinuclear chiral vanadium catalysts for oxidative coupling of 2-naphthols via a dual activation mechanism

Shinobu Takizawa et al.

CHEMICAL COMMUNICATIONS (2008)

Review Chemistry, Multidisciplinary

Synthesis and pharmacology of galantamine

J Marco-Contelles et al.

CHEMICAL REVIEWS (2006)

Article Chemistry, Medicinal

Efficient synthesis and structure-activity relationship of honokiol, a neurotrophic biphenyl-type neolignan

T Esumi et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2004)

Article Chemistry, Multidisciplinary

General approach for the synthesis of chiral perylenequinones via catalytic enantioselective oxidative biaryl coupling

CA Mulrooney et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)