4.8 Article

Copper-Catalyzed Enantioselective C-H Arylation between 2-Arylindoles and Hypervalent Iodine Reagents

Related references

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

Diols Activation by Cu/Borinic Acids Synergistic Catalysis in Atroposelective Ring-Opening of Cyclic Diaryliodoniums

Kun Zhao et al.

Summary: A Cu-catalyzed enantioselective ring-opening alkoxygenation reaction of cyclic diaryliodonium salts and diols was reported, with borinic acids playing a key role in selectively activating different types of diols. The proposed catalytic cycle involves a key ion pair model to account for the observed enantioselectivity. This study provides insights into the design of chiral catalysts for selective synthesis of cyclic molecules.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Atroposelective Construction of Indoles via C-H Bond Activation

Lincong Sun et al.

Summary: This study reports the rhodium(III)-catalyzed C-H activation of anilines bearing an N-isoquinolyl directing group for oxidative [3+2] annulation with four classes of internal alkynes, leading to atroposelective indole synthesis via dynamic kinetic annulation with C-N reductive elimination constituting the stereo-determining step. The reaction proceeds under mild conditions with high regio- and enantioselectivity and functional group compatibility.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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)

Article Chemistry, Organic

Construction of Atropisomeric 3-Arylindoles via Enantioselective Cacchi Reaction

Xiaojiao Li et al.

Summary: The de novo construction of axially chiral 3-arylindoles bearing a C(3)-C(aryl) chiral axis has been successfully achieved through a Pd-catalyzed enantioselective Cacchi reaction between aryl bromides and o-alkynylanilines. The reaction proceeds under mild conditions with high yields and excellent enantioselectivities.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

Asymmetric Synthesis of Axially Chiral Naphthyl-C3-indoles via a Palladium-Catalyzed Cacchi Reaction

Cong-Shuai Wang et al.

Summary: Atropoisomeric biaryl motifs are widely utilized in natural products and chiral catalysts. This study presents an efficient Pd(0)/(S)-Segphos-catalyzed atroposelective Cacchi reaction to construct a variety of naphthyl-C3-indoles with high yields and good to excellent atroposelectivities. The conformational stability of the obtained axially chiral naphthyl-C3-indole containing a synthetically more-valuable free NH moiety was revealed through kinetic experiments, highlighting the importance of water addition and manipulation procedure modulation for success.

ORGANIC LETTERS (2021)

Review Chemistry, Multidisciplinary

Organocatalytic Asymmetric Synthesis of Indole-Based Chiral Heterocycles: Strategies, Reactions, and Outreach

Yu-Chen Zhang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

Article Chemistry, Multidisciplinary

Chiral Phosphoric Acid Catalyzed Atroposelective C-H Amination of Arenes

Wang Xia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Enantioselective Cacchi Reaction: Asymmetric Synthesis of Axially Chiral 2,3-Disubstituted Indoles

Yu-Ping He et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of N-C Axially Chiral Compounds by Cu-Catalyzed Atroposelective Aryl Amination

Johanna Frey et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Multidisciplinary

Catalytic Asymmetric Construction of Axially Chiral Indole-Based Frameworks: An Emerging Area

Tian-Zhen Li et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

Atroposelective Ring Opening of Cyclic Diaryliodonium Salts with Bulky Anilines Controlled by a Chiral Cobalt(III) Anion

Xue Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Organic

Catalytic Asymmetric Synthesis of 3,3′-Bisindoles Bearing Single Axial Chirality

Ke-Wei Chen et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Editorial Material Chemistry, Organic

Design and Catalytic Asymmetric Construction of Axially Chiral Aryl-Alkene-Indole Frameworks

Bin Tan

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Rh(III)-Catalyzed Asymmetric Synthesis of Axially Chiral Biindolyls by Merging C-H Activation and Nucleophilic Cyclization

Miaomiao Tian et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Organocatalytic Asymmetric Annulation of ortho-Alkynylanilines: Synthesis of Axially Chiral Naphthyl-C2-indoles

Lei Peng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

A Strategy for Synthesizing Axially Chiral Naphthyl-Indoles: Catalytic Asymmetric Addition Reactions of Racemic Substrates

Fei Jiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade

Shenci Lu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Organic

Atroposelective Haloamidation of Indoles with Amino Acid Derivatives and Hypohalides

Zhaojie Li et al.

ORGANIC LETTERS (2019)

Article Chemistry, Multidisciplinary

Design and Catalytic Asymmetric Construction of Axially Chiral 3,3′-Bisindole Skeletons

Chun Ma et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Enantioselective organocatalytic activation of vinylidene-quinone methides (VQMs)

Jean Rodriguez et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Organocatalytic asymmetric arylation of indoles enabled by azo groups

Liang-Wen Qi et al.

NATURE CHEMISTRY (2018)

Review Chemistry, Multidisciplinary

Construction of Axially Chiral Compounds via Asymmetric Organocatalysis

Yong-Bin Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2018)

Article Chemistry, Multidisciplinary

Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes

Bin Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Physical

Catalyst-Controlled Stereoselective Synthesis of Atropisomers

Bouthayna Zilate et al.

ACS CATALYSIS (2018)

Article Chemistry, Multidisciplinary

Design and Enantioselective Construction of Axially Chiral Naphthyl-Indole Skeletons

Hong-Hao Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Organocatalytic Intramolecular [4+2] Cycloaddition between In Situ Generated Vinylidene ortho-Quinone Methides and Benzofurans

Xiaoyan Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

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

J. Wencel-Delord et al.

CHEMICAL SOCIETY REVIEWS (2015)

Article Chemistry, Multidisciplinary

Multiwfn: A multifunctional wavefunction analyzer

Tian Lu et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Synthesis of Atropisomeric Indoles with an N-C Chiral Axis

Nobutaka Ototake et al.

CHEMISTRY-A EUROPEAN JOURNAL (2010)

Article Chemistry, Multidisciplinary

Cu(II)-Catalyzed direct and site-selective arylation of indoles under mild conditions

Robert J. Phipps et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)