4.7 Article

General Method for the Amination of Aryl Halides with Primary and Secondary Alkyl Amines via Nickel Photocatalysis

Related references

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

Photochemically Enabled, Ni-Catalyzed Cyanation of Aryl Halides

Yonggang Yan et al.

Summary: A light-promoted Ni-catalyzed cyanation reaction using 1,4-dicyanobenzene as a cyanating agent is described. Various aryl bromides, chlorides, and druglike molecules are converted to their corresponding nitriles (65 examples). Mechanistic studies reveal that under irradiation, the Ni(II)(dtbbpy)(p-C6H4CN)(CN) oxidative addition product undergoes homolytic cleavage of the Ni-aryl bond to generate an aryl radical and a Ni(I)-CN species, which initiates subsequent cyanation reactions.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Light-Promoted C-N Coupling of Aryl Halides with Nitroarenes

Gang Li et al.

Summary: This study demonstrates a photochemical C-N coupling of aryl halides with nitroarenes for the first time, catalyzed by a Ni-II complex in the absence of any external photosensitizer. The method provides a step-economic extension to the widely used Buchwald-Hartwig C-N coupling reaction and tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest the reaction proceeds via the addition of an aryl radical, generated from a Ni-I/Ni-III cycle, to a nitrosoarene intermediate.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Photoactive Nickel Complexes in Cross-Coupling Catalysis

Oliver S. Wenger

Summary: Transition metal catalyzed cross-coupling reactions play a crucial role in chemical synthesis for forming C-C and C-heteroatom bonds. The combination of nickel catalysis with photoredox chemistry offers new synthetic possibilities, with electronically excited states of nickel complexes playing a key role. However, the potential of photoactive nickel complexes in organic synthesis still requires further exploration and development.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Review Chemistry, Multidisciplinary

Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp3)-H Cross-Coupling

Stavros K. Kariofillis et al.

Summary: In recent years, the development of light-driven reactions has made significant advancements in synthetic organic chemistry, particularly in combining photoredox and nickel catalysis for challenging cross-coupling reactions. The question of whether photo-induced activation of the nickel catalyst itself could lead to new approaches to cross-coupling has been explored. By utilizing a visible-light-driven mechanism for chlorine radical formation and conducting mechanistic investigations on organometallic Ni complexes relevant to cross-coupling, the study aims to facilitate new catalyst design and develop novel synthetic methods.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

Review Chemistry, Multidisciplinary

Visible-Light-Induced Homolysis of Earth-Abundant Metal-Substrate Complexes: A Complementary Activation Strategy in Photoredox Catalysis

Youssef Abderrazak et al.

Summary: The mainstream applications of visible-light photoredox catalysis mainly involve precious metal Ru-II or Ir-III complexes or organic dyes with low photostability. Earth-abundant metal-based (MLn)-L-n-type complexes are evolving rapidly as alternative photocatalysts that offer economic and ecological advantages and access to complementary inner-sphere mechanistic modes, transcending the inherent limitations of ultrashort excited-state lifetimes. The process of visible-light-induced homolysis (VLIH) involves the formation of light-absorbing ligated metal-substrate complexes that undergo homolytic cleavage for further transformations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Chiral Arylated Amines via C-N Coupling of Chiral Amines with Aryl Bromides Promoted by Light

Geyang Song et al.

Summary: The article introduces a method based on molecular Ni catalysis driven by light, allowing stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides without the need for any external photosensitizer. The method is effective for a wide variety of coupling partners with functional groups sensitive to bases and nucleophiles, providing a viable alternative for accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters, as shown by 92 examples with up to 99% ee.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Redox-Neutral Cross-Coupling Amination with Weak N-Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis

Chen Zhu et al.

Summary: A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described in this study. Various weak N-nucleophiles, including anilines, sulfonamides, etc., can be efficiently coupled with aryl halides and aryl tosylates via concerted paired electrolysis. Interestingly, the product selectivity toward the formation of amine and imine product can be addressed by a base switch when benzophenone imine is applied in the arylation.

JACS AU (2021)

Article Chemistry, Multidisciplinary

A Unified and Practical Method for Carbon-Heteroatom Cross-Coupling using Nickel/Photo Dual Catalysis

Randolph A. Escobar et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C-N Cross-Coupling

Richard Y. Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Transient Absorption Spectroscopy Offers Mechanistic Insights for an Iridium/Nickel-Catalyzed C-O Coupling

Lei Tian et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

General Paradigm in Photoredox Nickel-Catalyzed Cross-Coupling Allows for Light-Free Access to Reactivity

Rui Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex

Liu Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

3d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications

Stephen Ting et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Mechanistic Analysis of Metallaphotoredox C-N Coupling: Photocatalysis Initiates and Perpetuates Ni(I)/Ni(III) Coupling Activity

Nicholas A. Till et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

PAd2-DalPhos Enables the Nickel-Catalyzed C-N Cross-Coupling of Primary Heteroarylamines and (Hetero)aryl Chlorides

Jillian S. K. Clark et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Synthesis and Reactivity of Paramagnetic Nickel Polypyridyl Complexes Relevant to C(sp2)-C(sp3)Coupling Reactions

Megan Mohadjer Beromi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

Zhixiang Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications

Yu Kawamata et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Review Chemistry, Multidisciplinary

The Buchwald-Hartwig Amination After 25 Years

Ruth Dorel et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Applied

The 25th Anniversary of the Buchwald-Hartwig Amination: Development, Applications, and Outlook

Paola A. Forero-Cortes et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2019)

Article Chemistry, Multidisciplinary

Rational Design of Fluorogenic and Spontaneously Blinking Labels for Super-Resolution Imaging

Qinsi Zheng et al.

ACS CENTRAL SCIENCE (2019)

Article Chemistry, Multidisciplinary

Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C-N Cross-Coupling Reactions

Max Kudisch et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

PhPAd-DalPhos: Ligand-Enabled, Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Electrophiles with Bulky Primary Alkylamines

Joseph P. Tassone et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Elucidation of a Redox-Mediated Reaction Cycle for Nickel-Catalyzed Cross Coupling

Rui Sun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Practical heterogeneous photoredox/nickel dual catalysis for C-N and C-O coupling reactions

Yi-Yin Liu et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Taehoon Kim et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer

Benjamin J. Shields et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C-O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols

Preston M. MacQueen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

C-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes

Chern-Hooi Lim et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Agriculture, Multidisciplinary

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Ponnam Devendar et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2018)

Review Chemistry, Multidisciplinary

Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation

Subhajit Bhunia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Electrochemically Enabled, Nickel-Catalyzed Amination

Chao Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Biochemistry & Molecular Biology

Chemistry Is Dead. Long Live Chemistry!

Luke D. Lavis

BIOCHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Ni-Catalyzed Amination Reactions: An Overview

Mario Marin et al.

CHEMICAL RECORD (2016)

Review Chemistry, Multidisciplinary

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

Paula Ruiz-Castillo et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

Direct C(sp3)-H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals

Benjamin J. Shields et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Biochemical Research Methods

Photo-induced iodination of aryl halides under very mild conditions

Lu Li et al.

NATURE PROTOCOLS (2016)

Article Chemistry, Organic

Palladium-Catalyzed N-Arylation of Cyclopropylamines

Peter G. Gildner et al.

ORGANIC LETTERS (2016)

Article Multidisciplinary Sciences

Aryl amination using ligand-free Ni(II) salts and photoredox catalysis

Emily B. Corcoran et al.

SCIENCE (2016)

Article Multidisciplinary Sciences

Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design

Christopher M. Lavoie et al.

NATURE COMMUNICATIONS (2016)

Article Chemistry, Organic

An Air-Stable Nickel(0) Phosphite Precatalyst for Primary Alkylamine C-N Cross-Coupling Reactions

Sven S. Kampmann et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Organic

Pd-Catalyzed Diamination of 1,2,4-Triazinyl Complexant Scaffolds

Serene Tai et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis

Paula Ruiz-Castillo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

A Modular, Air-Stable Nickel Precatalyst

Jason D. Shields et al.

ORGANIC LETTERS (2015)

Editorial Material Chemistry, Physical

Nickel: The Spirited Horse of Transition Metal Catalysis

Valentine P. Ananikov

ACS CATALYSIS (2015)

Review Multidisciplinary Sciences

Recent advances in homogeneous nickel catalysis

Sarah Z. Tasker et al.

NATURE (2014)

Review Chemistry, Multidisciplinary

C-N bond forming cross-coupling reactions: an overview

Jitender Bariwal et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Medicinal

Diazaspirocyclic compounds as selective ligands for the α4β2 nicotinic acetylcholine receptor

Jon-Paul Strachan et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2012)

Article Chemistry, Multidisciplinary

Nickel-catalysed aromatic Finkelstein reaction of aryl and heteroaryl bromides

Alastair A. Cant et al.

CHEMICAL COMMUNICATIONS (2012)

Review Chemistry, Inorganic & Nuclear

The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions

Irina P. Beletskaya et al.

ORGANOMETALLICS (2012)

Article Chemistry, Multidisciplinary

Self-repairable copolymers that change color

Dhanya Ramachandran et al.

RSC ADVANCES (2012)

Article Chemistry, Organic

Synthesis of Rhodamines from Fluoresceins Using Pd-Catalyzed C-N Cross-Coupling

Jonathan B. Grimm et al.

ORGANIC LETTERS (2011)

Article Chemistry, Multidisciplinary

Copper-promoted N-cyclopropylation of anilines and amines by cyclopropylboronic acid

Sebastien Benard et al.

CHEMICAL COMMUNICATIONS (2010)

Article Chemistry, Medicinal

Oxetanes in Drug Discovery: Structural and Synthetic Insights

Georg Wuitschik et al.

JOURNAL OF MEDICINAL CHEMISTRY (2010)

Review Pharmacology & Pharmacy

Chloroquine and its analogs: A new promise of an old drug for effective and safe cancer therapies

V. Raja Solomon et al.

EUROPEAN JOURNAL OF PHARMACOLOGY (2009)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Ring-Opening Hydroacylation of Methylenecyclopropanes: Synthesis of γ,δ-Unsaturated Ketones from Aldehydes

Hiroki Taniguchi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Applied

A Rapid, Large-Scale Synthesis of a Potent Cholecystokinin (CCK) 1R Receptor Agonist

Jeffrey T. Kuethe et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2008)

Article Chemistry, Organic

Assembly of 4-aminoquinolines via palladium catalysis:: A mild and convenient alternative to SNAr methodology

Brandon J. Margolis et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Review Chemistry, Multidisciplinary

Synthesis and properties of cyclopropane-derived peptidomimetics

Andreas Reichelt et al.

ACCOUNTS OF CHEMICAL RESEARCH (2006)

Article Chemistry, Inorganic & Nuclear

Simple synthesis of CpNi(NHC)Cl complexes (Cp = cyclopentadienyl;: NHC=N-heterocyclic carbene)

RA Kelly et al.

ORGANOMETALLICS (2005)

Article Chemistry, Organic

Study of a new rate increasing Base effect in the palladium-catalyzed amination of aryl iodides

C Meyers et al.

JOURNAL OF ORGANIC CHEMISTRY (2004)

Review Chemistry, Multidisciplinary

Biosynthesis and metabolism of cyclopropane rings in natural compounds

LA Wessjohann et al.

CHEMICAL REVIEWS (2003)

Article Chemistry, Multidisciplinary

Copper-catalyzed halogen exchange in aryl halides: An aromatic Finkelstein reaction

A Klapars et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)