4.6 Article

Atroposelective Synthesis of 2,2′-Bis(arylamino)-1,1′-biaryls by Oxidative Iron(III)- and Phosphoric Acid-Catalyzed C-C Coupling of Diarylamines

Related references

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

Iron-Catalyzed Oxidative C-O and C-N Coupling Reactions Using Air as Sole Oxidant

Alexander Purtsas et al.

Summary: In this paper, the oxygenation and amination reactions of tertiary arylamines are described. The key steps of these coupling reactions involve iron-catalyzed oxidative C-O or C-N bond formation, which typically provide the desired products in high yields and with excellent regioselectivity. These transformations are carried out using hexadecafluorophthalocyanine-iron(II) (FePcF16) as catalyst, with the presence of an acid or base additive, and only require ambient air as the oxidant.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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)

Review Chemistry, Multidisciplinary

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

Jun Kee Cheng et al.

Summary: Atropisomerism is a stereochemical behavior exhibited by three-dimensional molecules with rotationally restricted sigma bonds, and compounds with atropisomerically chiral properties are increasingly utilized in fields where molecular asymmetry is influential. There is a steady demand for atroposelective synthesis, leading to conceptually novel and streamlined methods for expanding the structural diversity of atropisomers. This review summarizes key achievements in the stereoselective preparation of biaryl, heterobiaryl, and nonbiaryl atropisomers between 2015 and 2020, emphasizing synthetic strategies for each structural class and potential applications of atropochiral targets.

CHEMICAL REVIEWS (2021)

Review Chemistry, Multidisciplinary

Organic synthesis with the most abundant transition metal-iron: from rust to multitasking catalysts

Sujoy Rana et al.

Summary: Iron catalysis has been extensively studied and developed in the past decades due to its rich chemistry and diverse applications, making it suitable for various organic synthesis reactions and reducing environmental pollution.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Iron-Catalyzed Oxidative C-C Cross-Coupling Reaction of Tertiary Anilines with Hydroxyarenes by Using Air as Sole Oxidant

Alexander Purtsas et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Biochemistry & Molecular Biology

Iron-Catalyzed Synthesis, Structure, and Photophysical Properties of Tetraarylnaphthidines

Alexander Purtsas et al.

MOLECULES (2020)

Article Chemistry, Multidisciplinary

Structure and Reactivity of Aromatic Radical Cations Generated by FeCl3

Takahiro Horibe et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Organic

Traceless point-to-axial chirality exchange in the atropselective synthesis of biaryls/heterobiaryls

Thien T. Nguyen

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

An intermolecular C-H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines

Christian K. Rank et al.

CHEMICAL COMMUNICATIONS (2019)

Review Chemistry, Medicinal

Recent encounters with atropisomerism in drug discovery

Peter W. Glunz

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2018)

Article Chemistry, Multidisciplinary

Binaphthyl-Bipyridyl Cyclic Dyads as a Chiroptical Switch

Kazuto Takaishi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Electrochemistry

Direct Anodic Dehydrogenative Cross- and Homo-Coupling of Formanilides

Lara Schulz et al.

CHEMELECTROCHEM (2018)

Article Chemistry, Multidisciplinary

Synthesis of 1,1-and 2,2-Bicarbazole Alkaloids by Iron(III)-Catalyzed Oxidative Coupling of 2-and 1-Hydroxycarbazoles

Christian Bruetting et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Article Chemistry, Multidisciplinary

Iron-Catalyzed Oxidative C-C and N-N Coupling of Diarylamines and Synthesis of Spiroacridines

Raphael F. Fritsche et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Organic

Asymmetric Oxidative Coupling of Phenols and Hydroxycarbazoles

Houng Kang et al.

ORGANIC LETTERS (2017)

Article Chemistry, Organic

Aerobic oxidative homocoupling reaction of anilides using heterogeneous metal catalysts

Shigenobu Fujimoto et al.

TETRAHEDRON LETTERS (2017)

Article Chemistry, Multidisciplinary

Organocatalytic Atroposelective Arylation of 2-Naphthylamines as a Practical Approach to Axially Chiral Biaryl Amino Alcohols

Ye-Hui Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Iron-Catalyzed C-H Bond Activation

Rui Shang et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts

Carolina M. Avila et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Reagent- and Metal-Free Anodic C-C Cross-Coupling of Aniline Derivatives

Lara Schulz et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions

Paula Ruiz-Castillo et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Organic

Bronsted Acid Catalyzed Functionalization of Aromatic Alcohols through Nucleophilic Substitution of Hydroxyl Group

Abhishek Kumar Mishra et al.

JOURNAL OF ORGANIC CHEMISTRY (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)

Review Chemistry, Multidisciplinary

Iron Catalysis in Organic Synthesis

Ingmar Bauer et al.

CHEMICAL REVIEWS (2015)

Review Chemistry, Multidisciplinary

Recent advances and new concepts for the synthesis of axially stereoenriched biaryls

J. Wencel-Delord et al.

CHEMICAL SOCIETY REVIEWS (2015)

Review Chemistry, Multidisciplinary

Catalytic Kinetic Resolution of Biaryl Compounds

Gaoyuan Ma et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Article Chemistry, Multidisciplinary

Atroposelective Synthesis of Axially Chiral Biaryldiols via Organocatalytic Arylation of 2-Naphthols

Ye-Hui Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

Organocatalytic Strategies for the Synthesis of Axially Chiral Compounds

Giorgio Bencivenni

SYNLETT (2015)

Article Chemistry, Multidisciplinary

Enantioselective alpha-amination enabled by a BINAM-derived phase-transfer catalyst

H. M. Nelson et al.

CHEMICAL SCIENCE (2015)

Article Chemistry, Multidisciplinary

Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes

Scott E. Denmark et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Benzidine Rearrangement

Chandra Kanta De et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Organocatalytic Aryl-Aryl Bond Formation: An Atroposelective [3,3]-Rearrangement Approach to BINAM Derivatives

Gong-Qiang Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Review Chemistry, Multidisciplinary

Enantioselective Fluorescent Sensors: A Tale of BINOL

Lin Pu

ACCOUNTS OF CHEMICAL RESEARCH (2012)

Review Chemistry, Multidisciplinary

Occurrence, Biogenesis, and Synthesis of Biologically Active Carbazole Alkaloids

Arndt W. Schmidt et al.

CHEMICAL REVIEWS (2012)

Review Chemistry, Multidisciplinary

Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products

Gerhard Bringmann et al.

CHEMICAL REVIEWS (2011)

Article Chemistry, Medicinal

Revealing Atropisomer Axial Chirality in Drug Discovery

Steven R. LaPlante et al.

CHEMMEDCHEM (2011)

Review Chemistry, Multidisciplinary

C-H Activation for the Construction of C-B Bonds

Ibraheem A. I. Mkhalid et al.

CHEMICAL REVIEWS (2010)

Article Chemistry, Multidisciplinary

Enantioenriched Synthesis of C1-Symmetric BINOLs: Iron-Catalyzed Cross-Coupling of 2-Naphthols and Some Mechanistic Insight

Hiromichi Egami et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Review Chemistry, Multidisciplinary

The Challenge of Atropisomerism in Drug Discovery

Jonathan Clayden et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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

Meta halogenation of 1,3-disubstituted arenes via iridium-catalyzed arene borylation

Jaclyn M. Murphy et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Reversible photoswitchable axially chiral dopants with high helical twisting power

Quan Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Organic

Biaryl synthesis with control of axial chirality

Timothy W. Wallace

ORGANIC & BIOMOLECULAR CHEMISTRY (2006)

Review Chemistry, Multidisciplinary

Modified BINAP: The how and the why

M Berthod et al.

CHEMICAL REVIEWS (2005)

Review Chemistry, Multidisciplinary

Atroposelective synthesis of axially chiral biaryl compounds

G Bringmann et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Article Chemistry, Multidisciplinary

Lewis base activation of Lewis acids: Catalytic enantioselective allylation and propargylation of aldehydes

SE Denmark et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)