4.8 Article

Experimental and Computational Studies on Cobalt(I)-Catalyzed Regioselective Allylic Alkylation Reactions

Related references

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

Remote Stereocontrol of All-Carbon Quaternary Centers via Cobalt-Catalyzed Asymmetric Olefin Isomerization

Xianle Rong et al.

Summary: This study reports a cobalt-catalyzed desymmetric olefin isomerization to access 1-methylcyclohexenes bearing beta-quaternary stereocenters in a chemo-, site-, and stereoselective fashion. The gram-scale synthesis and stereoretentive transformations of spirocyclic products demonstrate the synthetic utility of this reaction. This research provides a valuable method for the synthesis of valuable chiral olefins.

CCS CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Ir-Catalyzed Asymmetric Allylic Alkylation of Dialkyl Malonates Enabling the Construction of Enantioenriched All-Carbon Quaternary Centers

Farbod A. Moghadam et al.

Summary: An enantioselective iridium-catalyzed allylic alkylation of malonates with trisubstituted allylic electrophiles to form all-carbon quaternary stereocenters is reported. This reaction proceeds at ambient temperature and enables the preparation of a wide range of enantioenriched products in up to 93% yield and 97% ee. The quaternary products can be readily converted to several valuable building blocks such as vicinal quaternary products and beta-quaternary acids.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Highly Regioselective Cobalt-Catalyzed Hydroboration of Internal Alkynes

Yan-Dong Zhang et al.

Summary: In this study, we developed new Co complexes with cyclopropane-based diphosphine ligands that can catalyze highly chemo-, regio-, and stereoselective hydroboration reactions of unsymmetrical internal alkynes. These reactions exhibit unusual regioselectivity, leading to the synthesis of trisubstituted alkenylborates and alkenes with different stereochemistry.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Investigating Oxidative Addition Mechanisms of Allylic Electrophiles with Low-Valent Ni/Co Catalysts Using Electroanalytical and Data Science Techniques

Tianhua Tang et al.

Summary: In this study, the critical oxidative addition mechanism of the ir-allyl-Co/Ni complex was investigated. It was found that Co(I)/Ni(I) species are responsible for the oxidative addition reaction. A coordination-ionization-type transition state mechanism was proposed, which was supported by computational and ligand structural analysis.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Physical

General and Practical Route to Diverse 1-(Difluoro)alkyl-3-aryl Bicyclo[1.1.1]pentanes Enabled by an Fe-Catalyzed Multicomponent Radical Cross-Coupling Reaction

Angel Renteria-Gomez et al.

Summary: This study presents a conceptually different approach to access diverse (fluoro)alkyl BCP-aryls through an iron-catalyzed multicomponent radical cross-coupling reaction. Experimental and computational mechanistic studies provide insights into the mechanism and ligand effects on C-C bond formation.

ACS CATALYSIS (2022)

Article Chemistry, Inorganic & Nuclear

Activator-free single-component Co(I)-catalysts for regio- and enantioselective heterodimerization and hydroacylation reactions of 1,3-dienes. New reduction procedures for synthesis of [L]Co(I)-complexes and comparison to in situ generated catalysts

Mahesh M. Parsutkar et al.

Summary: This paper presents a practical method for the synthesis and isolation of cobalt(I) bis-phosphine complexes and their use in Co(I)-catalyzed reactions. These complexes exhibit good catalytic activity in low-valent cobalt-catalyzed reactions and can be used in various reactions with sensitive substrates. Additionally, these complexes are useful for synthesizing rare cationic complexes, which show excellent catalytic performance.

DALTON TRANSACTIONS (2022)

Article Chemistry, Multidisciplinary

Highly Enantioselective Cobalt-Catalyzed (3+2) Cycloadditions of Alkynylidenecyclopropanes

Eduardo Da Concepcion et al.

Summary: This study demonstrates that low-valent cobalt complexes equipped with chiral ligands can efficiently promote highly enantioselective (3+2) cycloadditions, resulting in good yields and excellent enantiomeric ratios. A mechanistic discussion based on experimental and computational data suggests the involvement of Co-I/Co-III catalytic cycles in this process.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins

Xufang Liu et al.

Summary: A novel method for the synthesis of chiral cyclic olefins, specifically 1-methylcyclohexenes, was reported in this study, enabling the construction of chiral compounds with diversified functionalities. The synthetic utility of this method was demonstrated by the concise and enantioselective synthesis of a natural product, beta-bisabolene, and further derivatizations showcased the versatility of the reaction products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Review Chemistry, Multidisciplinary

Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts

Lars Susse et al.

Summary: Asymmetric allylic alkylation using transition metals offers an efficient strategy for generating quaternary stereocenters. Recent advancements have shown the potential of first-row transition metals as a cost-effective and potentially equally efficient alternative. This review highlights the use of different transition metals for catalyzing reactions with nucleophiles to assemble quaternary stereocenters.

CHEMICAL REVIEWS (2021)

Article Chemistry, Inorganic & Nuclear

Well-Defined Cationic Cobalt(I) Precatalyst for Olefin-Alkyne [2+2] Cycloaddition and Olefin-Diene Hydrovinylation Reactions: Experimental Evidence for Metallacycle Intermediates

Marcus E. Farmer et al.

Summary: This study describes the synthesis and characterization of a cationic cobalt(I) arene complex and evaluates its performance as a catalyst for carbon-carbon bond-forming reactions, demonstrating high catalytic activity and chemoselectivity.

ORGANOMETALLICS (2021)

Article Multidisciplinary Sciences

General method for iron-catalyzed multicomponent radical cascades-cross-couplings

Lei Liu et al.

Summary: Transition metal-catalyzed cross-coupling reactions are widely used in chemical synthesis. Iron (Fe) has potential advantages as a cheaper, more abundant, and less toxic catalyst, but its practical application in multicomponent cross-couplings remains challenging. Research demonstrates successful coupling of alpha-boryl radicals with Grignard reagents using 1,2-bis(dicyclohexylphosphino)ethane Fe-catalyzed reactions, and further development of a broadly applicable Fe-catalyzed multicomponent annulation-cross-coupling protocol.

SCIENCE (2021)

Article Chemistry, Multidisciplinary

Expedient Dual Co/Organophotoredox Catalyzed Stereoselective Synthesis of All-Carbon Quaternary Centers

Alex Cristofol et al.

Summary: An efficient Co/organophotoredox dual catalysis protocol has been developed for the stereoselective access to a wide variety of syn-configured 1,3-diols with quaternary carbon centers. Mechanistic control experiments suggest that the stereoselectivity is rationalized via a preferred Zimmerman-Traxler transition state. This newly developed process expands the use of base metal catalysis in constructing challenging quaternary carbon stereocenters.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Oscar Pamies et al.

Summary: This review covers the evolution, mechanistic understanding, and recent advances in enantioselective Pd-catalyzed allylic substitution, decarboxylative, and oxidative allylic substitutions. The catalytic data and examples of their application are collected, along with discussions on key mechanistic aspects for high selectivity and comparison with other metals. Different nucleophiles employed and ligand types for improved results in asymmetric allylic substitutions are highlighted.

CHEMICAL REVIEWS (2021)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Diastereo- and Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates

Lei Wang et al.

Summary: A novel cobalt-catalyzed reaction has been introduced in this article, which efficiently introduces allyl groups into molecules with stereoselective formation of diversified enantioenriched homoallylic alcohols. The mechanism involves allyl radical intermediates and represents a new strategy for enantioselective transformations using chiral Co complexes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Physical

Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of 1,6-Enynes: An Uncommon cis-β-C-H Activation Leads to Z-Selective Coupling of Acrylates

James H. Herbort et al.

Summary: Two intermolecular hydroalkenylation reactions of 1,6-enynes were demonstrated, leading to the formation of substituted 5-membered carbo- and heterocycles. The interactions of alkenes with a cobaltacyclopentene intermediate were found to be crucial, with unexpected beta-C-H activation observed in the case of acrylates. The reaction rate was dependent on the concentrations of cobalt, acrylate, and activator, indicating a complex mechanism involving multiple factors.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Electroreductive Cobalt-Catalyzed Carboxylation: Cross-Electrophile Electrocoupling with Atmospheric CO2

Nate W. J. Ang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes

Andrew Whyte et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Organic

Cobalt-Catalyzed Regio- and Enantioselective Allylic Alkylation of Malononitriles

Samir Ghorai et al.

ORGANIC LETTERS (2020)

Article Chemistry, Multidisciplinary

Enantioselective Cobalt-Catalyzed Intermolecular Hydroacylation of 1,6-Enynes

Andrew Whyte et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Organic

Recent advances in cobalt-catalyzed allylic functionalization

Jun-Fa Han et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible-Light Photoredox Catalysis

Miguel Claros et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Allylic Alkylation Enabled by Organophotoredox Catalysis

Koji Takizawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Syntheses and Catalytic Hydrogenation Performance of Cationic Bis(phosphine) Cobalt(I) Diene and Arene Compounds

Hongyu Zhong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Cationic Co(I)-Intermediates for Hydrofunctionalization Reactions: Regio- and Enantioselective Cobalt-Catalyzed 1,2-Hydroboration of 1,3-Dienes

Krishnaja Duvvuri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Regio- and Enantioselective Allylic Amination

Samir Ghorai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Intermolecular [2+2] Cycloaddition between Alkynes and Allenes

Wei Ding et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Iridium-Catalyzed Asymmetric Allylic Substitution Reactions

Qiang Cheng et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Vicinal All-Carbon Quaternary Centers via Iridium-Catalyzed Allylic Alkylation

J. Caleb Hethcox et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Multidisciplinary Sciences

Cobalt-catalyzed asymmetric hydrogenation of enamides enabled by single-electron reduction

Max R. Friedfeld et al.

SCIENCE (2018)

Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Tertiary Allylic Fluorides by Iridium-Catalyzed Allylic Fluoroalkylation

Trevor W. Butcher et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Allylic C(sp3)-H Carboxylation with CO2

Kenichi Michigami et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Hetero-dimerization of Acrylates and 1,3-Dienes

Stanley M. Jing et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Review Chemistry, Multidisciplinary

Applications of Iridium-Catalyzed Asymmetric Allylic Substitution Reactions in Target-Oriented Synthesis

Jianping Qu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Review Chemistry, Multidisciplinary

Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model

F. Matthias Bickelhaupt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic -Alkoxy Ketones

Xingyu Jiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons

Aijie Cai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Ligand-Controlled Divergent C-H Functionalization of Aldehydes with Enynes by Cobalt Catalysts

Rajagopal Santhoshkumar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates

Wenyong Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Regioselective Hydroacylation of 1,3-Dienes by Cobalt Catalysis

Qing-An Chen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Enantioselective Intramolecular Hydroacylation of Ketones and Olefins

Junfeng Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Article Chemistry, Organic

Achieving Control over the Branched/Linear Selectivity in Palladium-Catalyzed Allylic Amination

Igor Dubovyk et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Elimination/Isomerization of Enol Triflates into 1,3-Dienes

Ian T. Crouch et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Cobalt-Catalyzed Reductive Allylation of Alkyl Halides with Allylic Acetates or Carbonates

Xin Qian et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Catalytic asymmetric carbon-carbon bond formation via allylic alkylations with organolithium compounds

Manuel Perez et al.

NATURE CHEMISTRY (2011)

Review Chemistry, Multidisciplinary

Mechanistically Driven Development of Iridium Catalysts for Asymmetric Allylic Substitution

John F. Hartwig et al.

ACCOUNTS OF CHEMICAL RESEARCH (2010)

Article Chemistry, Multidisciplinary

Cobalt-catalyzed [2+2] cycloaddition

Jonas Treutwein et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Review Chemistry, Multidisciplinary

Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents

Syuzanna R. Harutyunyan et al.

CHEMICAL REVIEWS (2008)

Review Chemistry, Multidisciplinary

Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions

A. Alexakis et al.

CHEMICAL REVIEWS (2008)

Review Chemistry, Organic

Copper-catalyzed asymmetric allylic alkylation

Caroline A. Falciola et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2008)

Article Chemistry, Multidisciplinary

A highly effective phosphoramidite ligand for asymmetric allylic substitution

K Tissot-Croset et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

Review Chemistry, Multidisciplinary

Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis

BM Trost et al.

CHEMICAL REVIEWS (2003)

Review Chemistry, Multidisciplinary

Ligand bite angle effects in metal-catalyzed C-C bond formation

PWNM van Leeuwen et al.

CHEMICAL REVIEWS (2000)