4.8 Article

Enantio- and Regioselective Ni-Catalyzed para-C-H Alkylation of Pyridines with Styrenes via Intermolecular Hydroarylation

Related references

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

Chemo- and Enantioselective Arylation and Alkenylation of Aldehydes Enabled by Nickel/N-Heterocyclic Carbene Catalysis

Zi-Chao Wang et al.

Summary: In this study, the first highly enantioselective Ni-catalyzed arylation and alkenylation of simple aldehydes using readily available and stable organoboronic esters was reported. The protocol provides various chiral secondary alcohols with high yields and enantioselectivities, and has a broad scope of substrates, functional groups, and heterocycles.

CCS CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Enantioselective Ni/N-Heterocyclic Carbene-Catalyzed Redox-Economical Coupling of Aldehydes, Alkynes, and Enones for Rapid Construction of Acyclic All-Carbon Quaternary Stereocenters

Wu-Bin Zhang et al.

Summary: An innovative method for constructing acyclic quaternary carbon stereocenters from aldehydes, alkynes, and enones through N-heterocyclic carbene (NHC)-Ni catalysis has been successfully developed, with high selectivity and atom economy. This strategy is expected to inspire new and efficient approaches for generating other acyclic quaternary stereocenters.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Fast Enantio- and Chemoselective Arylation of Ketones with Organoboronic Esters Enabled by Nickel/N-Heterocyclic Carbene Catalysis

Yuan Cai et al.

Summary: This study reports a highly efficient NHC/Ni-catalyzed addition reaction of arylboronic esters to ketones, providing rapid access to chiral tertiary alcohols with broad substrate scope and excellent functional group tolerance. The reaction differs from other Ni-mediated reactions, exhibiting good specificity and tolerance to various functional groups.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Cp*Co(III)-Catalyzed Enantioselective Hydroarylation of Unactivated Terminal Alkenes via C-H Activation

Yan-Hua Liu et al.

Summary: The study reports a Cp*Co(III)-catalyzed asymmetric hydroarylation of unactivated aliphatic terminal alkenes assisted by tailor-made amino acid ligands. A novel noncovalent interaction was found critical for the chiral induction, resulting in high yields and excellent enantioselectivities of C2-alkylated indoles. DFT calculations revealed the reaction mechanism and origins of chiral induction in the stereodetermining alkene insertion step.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

A directive Ni catalyst overrides conventional site selectivity in pyridine C-H alkenylation

Tao Zhang et al.

Summary: This study reports a bifunctional N-heterocyclic carbene-ligated Ni-Al catalyst that can smoothly carry out the C3-H alkenylation of pyridines. This method provides a series of C3-alkenylated pyridines in yields ranging from 43-99% and with up to 98:2 C3 selectivity. It is effective for late-stage C3 alkenylation of diverse complex pyridine motifs in bioactive molecules, allowing various pyridine and heteroarene substrates to be used as the limiting reagent.

NATURE CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Low-Temperature Nickel-Catalyzed C-N Cross-Coupling via Kinetic Resolution Enabled by a Bulky and Flexible Chiral N-Heterocyclic Carbene Ligand

Zi-Chao Wang et al.

Summary: The use of a bulky yet flexible chiral N-heterocyclic carbene (NHC) ligand in low-temperature Ni-catalyzed C-N cross-coupling has achieved high enantioselectivity with low barriers. Computational studies show that the rotations of multiple sigma-bonds on the chiral ligand can adapt to the changing needs of catalytic processes, making this design widely applicable to diverse transition states for challenging metal-catalyzed asymmetric cross-coupling reactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Pyridine Derivatives as Biologically Active Precursors; Organics and Selected Coordination Complexes

Ezzat Khan

Summary: "Pyridine is an important heterocyclic compound with widespread applications in the medicinal market, particularly in the field of cancer treatment. Research on pyridine holds promise for addressing a variety of disease-related issues."

CHEMISTRYSELECT (2021)

Article Chemistry, Multidisciplinary

Enantioconvergent Arylation of Racemic Secondary Alcohols to Chiral Tertiary Alcohols Enabled by Nickel/N-Heterocyclic Carbene Catalysis

Yuan Cai et al.

Summary: The study revealed a novel method for upgrading simple racemic secondary alcohols to enantioenriched tertiary alcohols, using an NHC-nickel catalyst to achieve efficient asymmetric alcohol alpha-C-H arylation, followed by asymmetric addition of arylboronic esters after dehydrogenation. Mechanistic studies and control experiments were conducted to understand the exceptional control over chemo- and enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Multidisciplinary Sciences

A radical approach for the selective C-H borylation of azines

Ji Hye Kim et al.

Summary: A new strategy for the borylation of azines has been developed, utilizing stable and inexpensive amine-borane reagents in conjunction with photocatalysis. This approach allows for selective borylation of nitrogen-containing aromatic heterocycles through the formation of highly reactive boryl radicals, providing an alternative tactic for sp(2) carbon-boron bond assembly. The strong nucleophilic character of the amine-boryl radicals enables predictable and site-selective carbon-boron bond formation in azine structures, leading to the preparation of borylated materials that are otherwise difficult to access.

NATURE (2021)

Article Multidisciplinary Sciences

Construction 7-membered ring via Ni-Al bimetal-enabled C-H cyclization for synthesis of tricyclic imidazoles

Jiang-Fei Li et al.

Summary: The study demonstrates a novel approach for the direct construction of 7-membered rings via Ni-Al co-catalyzed unreactive C-H cyclization of benzoimidazoles with alkenes, yielding a series of tricyclic imidazoles. Transition metal-catalyzed C-H cyclization for medium-ring synthesis has been limited to reactive C-H bonds, presenting a challenge for activating unreactive C-H bonds.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Applied

Nickel/NHC-Catalyzed Enantioselective Cyclization of Pyridones and Pyrimidones with Tethered Alkenes

Di Shen et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Review Chemistry, Multidisciplinary

Chiral N-Heterocyclic Carbene Ligands Enable Asymmetric C-H Bond Functionalization

Jompol Thongpaen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Enantioselective Twofold C-H Annulation of Formamides and Alkynes without Built-in Chelating Groups

Hao Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Regio- and Enantioselective C-H Cyclization of Pyridines with Alkenes Enabled by a Nickel/N-Heterocyclic Carbene Catalysis

Wu-Bin Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

Enantioselective C-H Activation with Earth-Abundant 3d Transition Metals

Joachim Loup et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

A Bulky Chiral N-Heterocyclic Carbene Nickel Catalyst Enables Enantioselective C-H Functionalizations of Indoles and Pyrroles

Johannes Diesel et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst

Lichen Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Nickel/NHC-Catalyzed Asymmetric C-H Alkylation of Fluoroarenes with Alkenes: Synthesis of Enantioenriched Fluorotetralins

Yuan Cai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Enantioselective Aluminum-Free Alkene Hydroarylations through C-H Activation by a Chiral Nickel/JoSPOphos Manifold

Joachim Loup et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Enantioselective Markovnikov Protoboration of alpha-Olefins Enabled by a Buttressed N-Heterocyclic Carbene Ligand

Yuan Cai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Enantioselective Ni-Al Bimetallic Catalyzed exo-Selective C-H Cyclization of Imidazoles with Alkenes

Yin-Xia Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Enantioselective Pyridone C-H Functionalizations Enabled by a Bulky N-Heterocyclic Carbene Ligand

Johannes Diesel et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Direct ortho-C-H Aminoalkylation of 2-Substituted Pyridine Derivatives Catalyzed by Yttrium Complexes with N,N′-Diarylethylenediamido Ligands

Abhinanda Kundu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile

Michael W. Gribble et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Branch-Selective and Enantioselective Iridium-Catalyzed Alkene Hydroarylation via Anilide-Directed C-H Oxidative Addition

Simon Grelaud et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Multidisciplinary Sciences

Enantioselective C(sp(3))-H bond activation by chiral transition metal catalysts

Tyler G. Saint-Denis et al.

SCIENCE (2018)

Article Multidisciplinary Sciences

Catalytic enantioselective Minisci-type addition to heteroarenes

Rupert S. J. Proctor et al.

SCIENCE (2018)

Article Chemistry, Multidisciplinary

Recent advances in Ni-Al bimetallic catalysis for unreactive bond transformation

Yin-Xia Wang et al.

SCIENCE CHINA-CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Enantioselective Cobalt(III)-Catalyzed C-H Activation Enabled by Chiral Carboxylic Acid Cooperation

Fabio Pesciaioli et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Site-Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis

Shogo Okumura et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Mild and Regioselective Benzylic C-H Functionalization: Ni-Catalyzed Reductive Arylation of Remote and Proximal Olefins

Yuli He et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Asymmetric Iron-Catalyzed C-H Alkylation Enabled by Remote Ligand meta-Substitution

Joachim Loup et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Transition-Metal-Catalyzed C-H Alkylation Using Alkenes

Zhe Dong et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Multidisciplinary

C-H Functionalization of Azines

Kei Murakami et al.

CHEMICAL REVIEWS (2017)

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Transformations Involving C-H Bond Cleavage by Transition-Metal Complexes

Christopher G. Newton et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Hydroacylation of Styrenes with Simple Aldehydes: Reaction Development and Mechanistic Insights

Li-Jun Xiao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Asymmetric Alkylation of N-Sulfonylbenzamides with Vinyl Ethers via C-H Bond Activation Catalyzed by Hydroxoiridium/Chiral Diene Complexes

Miyuki Hatano et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

para-Selective Alkylation of Benzamides and Aromatic Ketones by Cooperative Nickel/Aluminum Catalysis

Shogo Okumura et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Inorganic & Nuclear

Chromium-Catalyzed Regioselective Hydropyridination of Styrenes

Yuexuan Li et al.

ORGANOMETALLICS (2016)

Article Multidisciplinary Sciences

Alcohols as alkylating agents in heteroarene C-H functionalization

Jian Jin et al.

NATURE (2015)

Article Chemistry, Multidisciplinary

Rh(I)-Bisphosphine-Catalyzed Asymmetric, Intermolecular Hydroheteroarylation of α-Substituted Acrylate Derivatives

Claire M. Filloux et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Enantioselective C-H Bond Addition of Pyridines to Alkenes Catalyzed by Chiral Half-Sandwich Rare-Earth Complexes

Guoyong Song et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Linear-Selective Hydroarylation of Unactivated Terminal and Internal Olefins with Trifluoromethyl-Substituted Arenes

Joseph S. Bair et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed C4-Selective Direct Alkylation of Pyridines

Takashi Andou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Inorganic & Nuclear

Metal-complexes of optically active amino- and imino-based pyridine ligands in asymmetric catalysis

Giorgio Chelucci

COORDINATION CHEMISTRY REVIEWS (2013)

Article Chemistry, Organic

The geometry and electronic structure of Aristolochic acid: possible implications for a frozen resonance

Sergio Manzetti et al.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Iridium-Catalyzed Intermolecular Asymmetric Hydroheteroarylation of Bicycloalkenes

Christo S. Sevov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

Radical-Based Regioselective C-H Functionalization of Electron-Deficient Heteroarenes: Scope, Tunability, and Predictability

Fionn O'Hara et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Multidisciplinary

Pd-catalyzed oxidative C-H/C-H cross-coupling of pyridines with heteroarenes

Bo Liu et al.

CHEMICAL SCIENCE (2013)

Article Chemistry, Multidisciplinary

Multiwfn: A multifunctional wavefunction analyzer

Tian Lu et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2012)

Article Chemistry, Multidisciplinary

Ligand-Promoted C-3 Selective C-H Olefination of Pyridines with Pd Catalysts

Mengchun Ye et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Multidisciplinary

Rare-Earth-Catalyzed C-H Bond Addition of Pyridines to Olefins

Bing-Tao Guan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Multidisciplinary

Selective C-4 Alkylation of Pyridine by Nickel/Lewis Acid Catalysis

Yoshiaki Nakao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

A strategy for C-H activation of pyridines: Direct C-2 selective alkenylation of pyridines by Nickel/Lewis acid catalysis

Yoshiaki Nakao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Multidisciplinary

Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation

Jared C. Lewis et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Highly efficient and enantioselective cyclization of aromatic imines via directed C-H bond activation

RK Thalji et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)