☆ 4.8 Article

Catalytic Undirected Meta-Selective C-H Borylation of Metallocenes

ADVANCED SCIENCE (2023)

Related references

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

Air-Stable Organoradical Boron Reagents

Zenghui Li et al.

Summary: A series of organoradical boron reagents were successfully synthesized through the key step of C-H borylation for the first time. These reagents showed air stability and could be stored for several months in the solid state. They were fully investigated through various analysis techniques and found to be suitable for Suzuki-Miyaura coupling reactions while retaining the carbon radical center. Additionally, they exhibited fluorescent properties and can potentially be used for the synthesis of luminescent organic radicals and other functionalized open-shell materials.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection
Article Chemistry, Multidisciplinary

An Iridium/Aluminum Cooperative Strategy for the beta-C(sp(3))-H Borylation of Saturated Cyclic Amines

Yusuke Kuroda et al.

Summary: Herein, an iridium/aluminum cooperative catalytic system has been reported for the beta-selective C-H borylation of saturated cyclic amines and lactams. An enantioselective variant has also been achieved using chiral aluminum catalysts, resulting in high stereocontrol in the formation of C-B bonds. Computational studies suggest that the formation of a Lewis pair with the substrates is crucial for lowering the energy of the rate-determining reductive elimination step.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection
Article Chemistry, Multidisciplinary

Synthesis of planar chiral ferrocenes via enantioselective remote C-H activation

Lan Zhou et al.

Summary: In this study, a modular platform for constructing planar chirality in 1,3-disubstituted ferrocenes/ruthenocenes via an enantioselective relay remote C-H activation strategy was developed. Various 1,3-disubstituted planar chiral metallocenes were prepared with high enantioselectivity (-96-. 99% e.e.). The resulting metallocenes can be easily derivatized for use as ligands and catalysts in asymmetric catalysis and as building blocks for other applications.

NATURE CHEMISTRY (2023)

Add to Collection
Article Chemistry, Multidisciplinary

Catalytic undirected borylation of tertiary C-H bonds in bicyclo[1.1.1]pentanes and bicyclo[2.1.1]hexanes

Isaac F. Yu et al.

Summary: This article describes a broadly applicable method for the synthesis of boron-substituted bicyclo[1.1.1]pentanes and (hetero)bicyclo[2.1.1]hexanes by an iridium-catalysed borylation of the bridgehead tertiary C-H bond. The reaction is highly selective for the formation of bridgehead boronic esters and compatible with a broad range of functional groups. It can be used for the late-stage modification of pharmaceuticals containing this substructure and the synthesis of novel bicyclic building blocks.

NATURE CHEMISTRY (2023)

Add to Collection
Article Multidisciplinary Sciences

Remote steric control for undirected meta-selective C-H activation of arenes

Boobalan Ramadoss et al.

Summary: Regioselective functionalization of arenes is a challenging problem in organic synthesis. This study presents a strategy based on remote steric control, where a roof-like ligand protects the distant para site and enables selective activation of meta carbon-hydrogen (C-H) bonds.

SCIENCE (2022)

Add to Collection
Article Chemistry, Physical

Chiral Bidentate Boryl Ligand-Enabled Iridium-Catalyzed Enantioselective Dual C-H Borylation of Ferrocenes: Reaction Development and Mechanistic Insights

Xiaoliang Zou et al.

Summary: Ferrocenes with planar chirality are important for various chiral ligands and organocatalysts. This study reports an iridium-catalyzed enantioselective dual C-H borylation of ferrocenes using an amide directing group. The reaction showed high enantioselectivity and tolerance towards different functional groups.

ACS CATALYSIS (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Iridium-Catalyzed C(sp3)-H Borylation Using Silyl-Bipyridine Pincer Ligands

Ryohei Kawazu et al.

Summary: New ligands have been discovered for iridium-catalyzed C(sp(3))-H borylation of aliphatic compounds. A phenanthroline-based NNSi pincer ligand has shown excellent performance and enables efficient conversion of aliphatic compounds to borylated products using an Ir/NNSi pincer catalyst system.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Sterically Controlled Late-Stage Functionalization of Bulky Phosphines

Hao Deng et al.

Summary: This article introduces a novel method for fine-tuning phosphine ligands, which enables diversification of phosphine compounds by introducing different substituents into previously inaccessible positions. Compared to existing methods, this approach overcomes the limitations of phosphorus-directed reactions.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Add to Collection
Article Multidisciplinary Sciences

Electrochemically driven regioselective C-H phosphorylation of group 8 metallocenes

Hao Zheng et al.

Summary: This study reports an electrochemically driven method for the efficient synthesis of phosphorylated metallocenes, providing guidance for the C-H functionalization of symmetric metallocenes.

NATURE COMMUNICATIONS (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Remote Editing of Stacked Aromatic Assemblies for Heteroannular C-H Functionalization by a Palladium Switch between Aromatic Rings

Zhiqian Yu et al.

Summary: In this study, we present a new approach allowing remote editing of stacked aromatic assemblies through the use of a transient ligand as a bridge. Our results demonstrate the successful heteroannular C-H functionalization and uncover a unique reaction mechanism involving olefin coordination.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection
Review Chemistry, Multidisciplinary

Recent Advances in Transition-Metal-Catalyzed C-H Functionalization of Ferrocene Amides

Qi Mou et al.

Summary: In the field of synthetic organic chemistry, directing-group-assisted C-H functionalization has been found to be a key tool for the efficient and site-selective construction of C-C and hybrid bonds. Among the C-H functionalization of ferrocene derivatives, the directed group strategy using ferrocene amides is the most commonly used method due to its ease of synthesis and the fine, tuneable, and reversible coordination permitted by its metal center. This review extensively discusses various C-H bond functionalization reactions of ferrocene using amide directing groups.

CHEMISTRY-AN ASIAN JOURNAL (2022)

Add to Collection
Review Chemistry, Organic

Recent advances in the synthesis of ferrocene derivatives via 3d transition metal-catalyzed C-H functionalization

Zhuo-Zhuo Zhang et al.

Summary: In recent years, transition-metal-catalyzed C-H functionalization has become a powerful tool for synthesizing ferrocenes. However, using affordable and sustainable 3d metals in this process remains challenging. This paper summarizes the significant progress in 3d transition metal-catalyzed C-H activation for the synthesis of ferrocenes until December 2021.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Add to Collection
Article Chemistry, Multidisciplinary

Photo-induced catalytic C-H heteroarylation of 8 metallocenes

Gu-Chen He et al.

Summary: In this study, an efficient catalytic protocol for C-H heteroarylation of group 8 metallocenes (M = Fe, Ru) under light irradiation is reported. This intermolecular cross coupling exhibits directing group free, mild conditions, and a wide substrate scope.

CELL REPORTS PHYSICAL SCIENCE (2022)

Add to Collection
Article Chemistry, Organic

Ligand-Driven Advances in Iridium-Catalyzed sp3 C-H Borylation: 2,2′-Dipyridylarylmethane

Margaret R. Jones et al.

Summary: The field of catalytic C-H borylation has witnessed significant growth, offering a versatile approach for the preparation of organoborane products. While sp(2) C-H borylation methods are widely used, sp(3) C-H borylation reactions face challenges such as incomplete consumption of diboron reagents and harsh reaction conditions. Recent research has shown that utilizing dipyridylarylmethane ligands in sp(3) C-H borylation can overcome these challenges and contribute to the field.

SYNLETT (2021)

Add to Collection
Review Chemistry, Inorganic & Nuclear

Recent advances in the development of ferrocene based electroactive small molecules for cation recognition: A comprehensive review of the years 2010-2020

Adwitiya Pal et al.

Summary: Ferrocene-based electroanalytical sensors have shown significant progress in the past decade, enabling detection of various metal cations with favorable electrochemical properties, emission profiles, binding units, and stoichiometries. A comprehensive review has been conducted on 172 ligands and their interactions with different metal ions, presenting changes in output signals in tabular format. This review aims to assist the chemistry community in developing more effective electrochemical chemosensors in the future.

COORDINATION CHEMISTRY REVIEWS (2021)

Add to Collection
Article Chemistry, Multidisciplinary

Enantioselective C-H Alkenylation of Ferrocenes with Alkynes by Half-Sandwich Scandium Catalyst

Shao-Jie Lou et al.

Summary: The study demonstrates the highly enantioselective C-H alkenylation of quinoline- and pyridine-substituted ferrocenes with alkynes using a half-sandwich scandium catalyst. This method offers broad substrate scope, high enantioselectivity, and selectively affords a new family of planar-chiral ferrocenes bearing N/alkene functionalities. The use of a quinoline/alkene-functionalized ferrocene product as a chiral ligand for asymmetric catalysis is also showcased.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection
Article Chemistry, Multidisciplinary

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Md Emdadul Hoque et al.

Summary: A new class of C-H borylation catalysts with excellent reactivity and ortho-selectivity for aromatic substrates have been discovered, as well as efficient C(sp(3))-H bond borylations for aliphatic substrates. These catalysts also enable late-stage C-H functionalization and selective borylation of heterocyclic molecules, demonstrating their potential for broad application in C-H functionalization chemistry.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection
Review Chemistry, Multidisciplinary

Recent advances in asymmetric borylation by transition metal catalysis

Jiefeng Hu et al.

Summary: Researchers have devoted much effort in exploring synthetic methodologies for the preparation of chiral organoboronates. Among the known methods, asymmetric catalysis has emerged as a practical and highly efficient strategy for their straightforward preparation, with recent remarkable advances in approaches such as asymmetric borylative addition, asymmetric allylic borylation, and stereospecific cross-coupling borylation employing transition-metal catalysis with a chiral ligand.

CHEMICAL SOCIETY REVIEWS (2021)

Add to Collection
Review Chemistry, Organic

Recent Progress in Iridium-Catalyzed Remote Regioselective C-H Borylation of (Hetero)Arenes

Xiaoliang Zou et al.

Summary: (Hetero)Aryl boronic acids and their derivatives are widely used in synthetic chemistry, material sciences, and drug discovery, leading to a great deal of attention in developing novel synthetic methods for these structures. Ir-catalyzed C-H borylation is considered to be one of the most efficient methods, but the challenge lies in the regioselectivity control due to the restriction of the reaction mechanism. Recent progress in Ir-catalyzed remote selective C-H borylation of arenes is systematically discussed in this review.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection
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)

Add to Collection
Article Multidisciplinary Sciences

Diverse functionalization of strong alkyl C-H bonds by undirected borylation

Raphael Oeschger et al.

SCIENCE (2020)

Add to Collection
Article Chemistry, Multidisciplinary

Iridium-Catalyzed sp3 C-H Borylation in Hydrocarbon Solvent Enabled by 2,2′-Dipyridylarylmethane Ligands

Margaret R. Jones et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Add to Collection
Review Chemistry, Applied

A Review on the Latest Progress of Chan-Lam Coupling Reaction

Jin-Quan Chen et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Add to Collection
Article Chemistry, Physical

Achiral CpxIr(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C-H Amidation of Ferrocenes under Mild Conditions

Lei Liu et al.

ACS CATALYSIS (2020)

Add to Collection
Review Chemistry, Multidisciplinary

Asymmetric C-H Bond Functionalization of Ferrocenes: New Opportunities and Challenges

Chen-Xu Liu et al.

TRENDS IN CHEMISTRY (2020)

Add to Collection
Article Chemistry, Multidisciplinary

8-Aminoquinoline-Assisted Synthesis and Crystal Structure Studies of Ferrocenyl Aryl Sulfones

Moh Sattar et al.

CHEMISTRY-AN ASIAN JOURNAL (2019)

Add to Collection
Article Chemistry, Multidisciplinary

Rhodium-Catalyzed PIII-Directed ortho-C-H Borylation of Arylphosphines

Jian Wen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection
Article Chemistry, Multidisciplinary

PdII-Catalyzed Regio- and Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction between Ferrocenes and Azoles

Zhong-Jian Cai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Add to Collection
Article Chemistry, Organic

Copper-Catalyzed 8-Aminoquinoline Assisted Aryl Chalcogenation of Ferroceneamide with Aryl Disulfides, Diselenides, and Ditellurides

Moh. Sattar et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Add to Collection
Article Chemistry, Inorganic & Nuclear

Ferroceneboronic Acid and Derivatives: Synthesis, Structure, Electronic Properties, and Reactivity in Directed C-H Bond Activation

William Erb et al.

ORGANOMETALLICS (2018)

Add to Collection
Article Chemistry, Multidisciplinary

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism Inspired Solution to Boronic Ester Reactivity

Julien C. Vantourout et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Add to Collection
Review Chemistry, Medicinal

Recent Advances of Metallocenes for Medicinal Chemistry

Miguel M. Santos et al.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2017)

Add to Collection
Article Chemistry, Multidisciplinary

Borylation, silylation and selenation of C-H bonds in metal sandwich compounds by applying a directing group strategy

Mayukh Deb et al.

NEW JOURNAL OF CHEMISTRY (2017)

Add to Collection
Article Chemistry, Organic

Sulfur-Directed Ligand-Free C-H Borylation by Iridium Catalysis

Li Liu et al.

ORGANIC LETTERS (2017)

Add to Collection
Article Chemistry, Organic

Recent advances in catalytic C-H borylation reactions

Liang Xu et al.

TETRAHEDRON (2017)

Add to Collection
Review Chemistry, Multidisciplinary

Synthesis of Planar Chiral Ferrocenes via Transition-Metal-Catalyzed Direct C-H Bond Functionalization

De-Wei Gao et al.

ACCOUNTS OF CHEMICAL RESEARCH (2017)

Add to Collection
Review Chemistry, Physical

Synthesis of Planar Chiral Ferrocenes by Transition-Metal-Catalyzed Enantioselective C-H Activation

Dao-Yong Zhu et al.

CHEMCATCHEM (2016)

Add to Collection
Review Chemistry, Multidisciplinary

Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse

Emily C. Neeve et al.

CHEMICAL REVIEWS (2016)

Add to Collection
Review Chemistry, Multidisciplinary

Polymers with pendant ferrocenes

Rudolf Pietschnig

CHEMICAL SOCIETY REVIEWS (2016)

Add to Collection
Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Enantioselective Intramolecular CH Silylation for the Syntheses of Planar-Chiral Metallocene Siloles

Qing-Wei Zhang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Add to Collection
Article Chemistry, Multidisciplinary

Enantioselective synthesis of planar-chiral benzosiloloferrocenes by Rh-catalyzed intramolecular C-H silylation

Takanori Shibata et al.

CHEMICAL COMMUNICATIONS (2015)

Add to Collection
Review Chemistry, Multidisciplinary

Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules

Liang Xu et al.

CHEMICAL SOCIETY REVIEWS (2015)

Add to Collection
Article Chemistry, Multidisciplinary

Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation

Guanghui Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Add to Collection
Article Chemistry, Multidisciplinary

Iridium-Catalyzed Enantioselective C H Alkylation of Ferrocenes with Alkenes Using Chiral Diene Ligands**

Takanori Shibata et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Add to Collection
Article Chemistry, Multidisciplinary

Iridium-Catalyzed C-H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism

Matthew A. Larsen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Add to Collection
Article Chemistry, Multidisciplinary

Palladium-Catalyzed Intramolecular Asymmetric C-H Functionalization/Cyclization Reaction of Metallocenes: An Efficient Approach toward the Synthesis of Planar Chiral Metallocene Compounds

Ruixian Deng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Add to Collection
Article Chemistry, Multidisciplinary

Regioselective Borylation of the C-H Bonds in Alkylamines and Alkyl Ethers. Observation and Origin of High Reactivity of Primary C-H Bonds Beta to Nitrogen and Oxygen

Qian Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Add to Collection
Article Chemistry, Multidisciplinary

Enantioselective Synthesis of Planar Chiral Ferrocenes via Palladium-Catalyzed Direct Coupling with Arylboronic Acids

De-Wei Gao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Add to Collection
Article Chemistry, Multidisciplinary

Iridium-Catalyzed C-H Borylation of Cyclopropanes

Carl W. Liskey et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Add to Collection
Review Chemistry, Inorganic & Nuclear

A New Age for Iron: Antitumoral Ferrocenes

Susana S. Braga et al.

ORGANOMETALLICS (2013)

Add to Collection
Article Chemistry, Inorganic & Nuclear

Large-Scale Preparation of 1,1′-Ferrocenedicarboxylic Acid, a Key Compound for the Synthesis of 1,1′-Disubstituted Ferrocene Derivatives

Alex R. Petrov et al.

ORGANOMETALLICS (2013)

Add to Collection
Article Chemistry, Multidisciplinary

Redox of ferrocene controlled asymmetric dehydrogenative Heck reaction via palladium-catalyzed dual C-H bond activation

Chao Pi et al.

CHEMICAL SCIENCE (2013)

Add to Collection
Article Chemistry, Multidisciplinary

Acceptor-Substituted Ferrocenium Salts as Strong, Single-Electron Oxidants: Synthesis, Electrochemistry, Theoretical Investigations, and Initial Synthetic Application

Dushant A. Khobragade et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Add to Collection
Article Chemistry, Multidisciplinary

Iridium-Catalyzed Borylation of Secondary C-H Bonds in Cyclic Ethers

Carl W. Liskey et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Add to Collection
Review Chemistry, Multidisciplinary

Regioselectivity of the borylation of alkanes and arenes

John F. Hartwig

CHEMICAL SOCIETY REVIEWS (2011)

Add to Collection
Review Chemistry, Organic

Copper-Promoted Carbon-Heteroatom Bond Cross-Coupling with Boronic Acids and Derivatives

Jennifer X. Qiao et al.

SYNTHESIS-STUTTGART (2011)

Add to Collection
Article Chemistry, Multidisciplinary

Synthesis of rhazinicine by a metal-catalyzed C - H bond functionalization strategy

Elizabeth M. Beck et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

Add to Collection
Article Chemistry, Multidisciplinary

Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation

Sulagna Paul et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Add to Collection
Review Chemistry, Multidisciplinary

Asymmetric catalysis with planar-chiral derivatives of 4-(dimethylamino)pyridine

GC Fu

ACCOUNTS OF CHEMICAL RESEARCH (2004)

Add to Collection
Article Chemistry, Multidisciplinary

Ir-catalyzed C-H activation in the synthesis of borylated ferrocenes and half sandwich compounds

A Datta et al.

CHEMICAL COMMUNICATIONS (2004)

Add to Collection
Article Chemistry, Organic

Ferrocenyl monophosphine ligands: Synthesis and applications in the Suzuki-Miyaura coupling of aryl chlorides

C Baillie et al.

JOURNAL OF ORGANIC CHEMISTRY (2004)

Add to Collection
Article Chemistry, Applied

Iridium-catalyzed direct borylation of five-membered heteroarenes by bis(pinacolato)diboron: Regioselective, stoichiometric, and room temperature reactions

T Ishiyama et al.

ADVANCED SYNTHESIS & CATALYSIS (2003)

Add to Collection
Review Chemistry, Multidisciplinary

Asymmetric catalysis with chiral ferrocene ligands

LX Dai et al.

ACCOUNTS OF CHEMICAL RESEARCH (2003)

Add to Collection
Article Chemistry, Multidisciplinary

Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate

T Ishiyama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)

Add to Collection
Article Chemistry, Multidisciplinary

Electronic detection of single-base mismatches in DNA with ferrocene-modified probes

CJ Yu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Add to Collection
Webinars Posters Questions Hubs Funding Journals Papers Connect Collections Reviewers About Us FAQs Mobile App Privacy Policy Terms of Use
© Peeref 2019-2024. All rights reserved.