☆ 4.8 Article

Copper-Catalyzed Regio- and Enantioselective Hydroboration of Difluoroalkyl-Substituted Internal Alkenes

ADVANCED SCIENCE (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Multidisciplinary

Ligand-enabled stereodivergence in nickel-catalyzed regioselective hydroboration of internal allenes

Xiaoxu Yang et al.

Summary: The development of protocols for stereodivergent synthesis of multi-substituted alkenylboronates simplifies and unifies the synthesis of Z and E stereoisomers of multi-substituted alkenes. Although various efforts have been made to achieve stereoselective approaches to access Z or E alkenylboronates, catalyst-controlled stereodivergence in their synthesis is still rare. This study demonstrates that stereodivergence can be achieved for nickel-catalyzed hydroboration of internal allenes, enabling the convenient synthesis of both stereoisomers of trisubstituted alkenylboronates.

CHEM (2023)

添加到收藏夹

Review Chemistry, Multidisciplinary

Biological Utility of Fluorinated Compounds: from Materials Design to Molecular Imaging, Therapeutics and Environmental Remediation

Cheng Zhang et al.

Summary: This review discusses the applications of fluorinated molecules in bioengineering and nanotechnology, with a focus on controlling fluorine-fluorine interactions and understanding their impact on biological behavior. The controlled introduction of fluorine and its interactions can provide advantages in imaging, therapeutics, and environmental applications.

CHEMICAL REVIEWS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

A Fruitful Decade of Organofluorine Chemistry: New Reagents and Reactions

Feng-Ling Qing et al.

Summary: The development of synthetic methods for introducing fluorine atoms and fluoroalkyl groups into organic molecules has received increased attention. Synthetic organic chemists have made significant contributions in the field of organofluorine chemistry and the newly developed methods are typically safer and more effective than traditional methods.

CCS CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Remote Stereocenter through Amide-Directed, Rhodium-Catalyzed Enantioselective Hydroboration of Unactivated Internal Alkenes

Wei Zhao et al.

Summary: This study presents an amide-directed, rhodium-catalyzed highly diastereo- and enantioselective hydroboration reaction which provides a facile access to enantioenriched amines containing beta,gamma-vicinal stereocenters. Computational studies indicate that migratory insertion of the alkene into rhodium hydride controls the enantioselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates

Ming Hu et al.

Summary: Selective defluoroborylation and asymmetric hydro-boration reactions have been developed for fluoroalkyl-substituted terminal alkenes, resulting in the synthesis of chiral alkylboronates with fluoroalkyl-substituted stereogenic carbon centers.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed sp2/sp3 Diborylation of 1-Chloro-1-Trifluoromethylalkenes

Zhenwei Fan et al.

Summary: This study reveals an enantioselective Cu-catalyzed diborylation of 1-chloro-1-trifluoromethylalkenes, leading to diborylated compounds with a gem-difluoroalkenyl moiety. Notably, the newly formed C-B bonds include a stereoselective and optically pure Csp(3)-B bond.

ACS CENTRAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Organic

Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes

Yuki Kojima et al.

Summary: A copper-catalyzed regio- and stereoselective allylboration reaction has been developed to functionalize 1-trifluoromethylalkenes with bis(pinacolato)diboron and allylic chlorides, resulting in high diastereoselective trifluoromethylated products. The success of this reaction relies on the careful selection of Cs2CO3 base and t-Bu-modified dppe-type ligand, which allows for efficient catalyst turnover and suppression of defluorination side reactions. The resulting Bpin moiety can be derivatized to provide diverse CF3-containing molecules with high stereochemical fidelity.

ORGANIC LETTERS (2022)

添加到收藏夹

Review Chemistry, Organic

Transition Metal Catalyzed Asymmetric Hydroboration of Internal Alkenes

Lu Houxiang et al.

Summary: Transition metal catalyzed asymmetric hydroboration of alkenes is a powerful method for preparing chiral organoboronates, offering advantages such as simple raw materials, high atomic economy, and diverse borated product structures.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

The transition metal-catalysed hydroboration reaction

Stephen J. Geier et al.

Summary: The catalytic addition of hydridoboranes to unsaturated organic molecules using transition metals has gained significant attention and has seen rapid development and wide application in recent years. This reaction can not only be used in organic synthesis, but also as a method for assessing catalyst activity and reactivity.

CHEMICAL SOCIETY REVIEWS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Recent Advances in the Construction of Fluorinated Organoboron Compounds

Xingxing Ma et al.

Summary: This review provides guidance on the research of fluorinated organoboron compounds, focusing on selective monodefluoro-borylation of polyfluoroarenes and polyfluoroalkenes, selective borylation of fluorinated substrates, selective fluorination of organoboron compounds, and borofluorination of alkynes/olefins.

JACS AU (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Regio- and enantioselective umpolung gem-difluoroallylation of hydrazones via palladium catalysis enabled by N-heterocyclic carbene ligand

Shuai Huang et al.

Summary: This study presents a method for difluoroallylation of hydrazones via palladium and N-heterocyclic carbene catalysis, yielding products with high yields and selectivities. The use of chiral N-heterocyclic carbene as a ligand is crucial for enhancing selectivities and reaction productivity.

NATURE COMMUNICATIONS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Recent progress in cobalt-catalyzed enantioselective hydrogenation and hydroboration reactions of alkenes

Xiaoxu Yang et al.

Summary: Recent studies have shown that cobalt catalysts in transition metal-catalyzed asymmetric hydrofunctionalization of alkenes have rapidly developed and demonstrated comparable or even better catalytic performance than their rhodium counterparts. Cobalt compounds have broad application prospects in asymmetric hydrogenation and hydroboration of alkenes, with ongoing discussions on the mechanisms involved.

CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Copper-Catalyzed Highly Selective Protoboration of CF3-Containing 1,3-Dienes

Juanjuan Wu et al.

Summary: The study presents a copper-catalyzed highly selective protoboration reaction that can suppress defluorination and provide CF3-containing borated reagents. Functional group tolerance of this reaction is well demonstrated, with the products serving as versatile precursors for various transformations. By using a chiral diphosphine ligand, allylic boron reagents with a CF3-containing chiral center were synthesized for the first time. Additionally, in-depth DFT calculations were conducted to understand the mechanism behind the inhibition of defluorination.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Multidisciplinary Sciences

Contemporary synthetic strategies in organofluorine chemistry

Robert Britton et al.

Summary: Fluorinated molecules have various applications, with fluorination and fluoroalkylation being the main strategies for constructing carbon-fluorine and fluorinated carbon-carbon bonds. Rapid growth in fluorination and fluoroalkylation methods has been witnessed in the past two decades due to the development of new reagents and catalysts, and further landmark achievements are expected in everyday applications as organofluorine compounds are increasingly used.

NATURE REVIEWS METHODS PRIMERS (2021)

添加到收藏夹

Article Chemistry, Organic

Catalytic Asymmetric Conjugate Protosilylation and Protoborylation of 2-Trifluoromethyl Enynes for Synthesis of Functionalized Allenes

Chao Yang et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition

Richard Y. Liu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Regio- and Enantioselective Bromocyclization of Difluoroalkenes as a Strategy to Access Tetrasubstituted Difluoromethylene-Containing Stereocenters

Edward Miller et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Contribution of Organofluorine Compounds to Pharmaceuticals

Munenori Inoue et al.

ACS OMEGA (2020)

添加到收藏夹

Article Chemistry, Organic

An Asymmetric Suzuki-Miyaura Approach to Prostaglandins: Synthesis of Tafluprost

Roman Kucera et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Stereospecific 1,2-Migrations of Boronate Complexes Induced by Electrophiles

Hui Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Cu-Catalyzed Regio- and Stereodivergent Chemoselective sp2/sp3 1,3-and 1,4-Diborylations of CF3-Containing 1,3-Enynes

Zhijie Kuang et al.

CHEM (2020)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Defluorinative Borylation and Silylation of gem-Difluoroallyl Groups

Trevor W. Butcher et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Organic

Catalytic Enantioselective Synthesis of Difluoromethylated Tetrasubstituted Stereocenters in Isoindolones Enabled by a Multiple-Fluorine System

Meng-Yu Rong et al.

ORGANIC LETTERS (2020)

添加到收藏夹

Article Chemistry, Organic

Ligand-controlled copper-catalyzed 1,2 or 1,4-protoborylation of 2-trifluoromethyl-1,3-conjugated enynes

Jialu Li et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereodivergent Synthesis through Catalytic Asymmetric Reversed Hydroboration

Tao-Tao Gao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives

Sota Akiyama et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Copper-Catalyzed Highly Enantioselective Difluoroalkylation of Secondary Propargyl Sulfonates with Difluoroenoxysilanes

Xing Gao et al.

CHEM (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Boryl and Silyl Substitution with Trifluoromethyl Alkenes: Scope, Utility, and Mechanistic Nuances of Cu-F β-Elimination

Paulo H. S. Paioti et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration

Suman Chakrabarty et al.

CHEMICAL SCIENCE (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Catalytic selective mono- and difluoroalkylation using fluorinated silyl enol ethers

Xiao-Si Hu et al.

CHEMICAL COMMUNICATIONS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Copper(I)-Catalyzed Enantioselective -Boryl Substitution of Trifluoromethyl-Substituted Alkenes: Synthesis of Enantioenriched gamma,gamma-gem-Difluoroallylboronates

Ryoto Kojima et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs

Yi Zhu et al.

CHEMICAL REVIEWS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents

Minyan Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

添加到收藏夹

Article Medicine, General & Internal

Glecaprevir-Pibrentasvir for 8 or 12 Weeks in HCV Genotype 1 or 3 Infection

S. Zeuzem et al.

NEW ENGLAND JOURNAL OF MEDICINE (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Earth-abundant transition metal catalysts for alkene hydrosilylation and hydroboration

Jennifer V. Obligacion et al.

NATURE REVIEWS CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Physical

Cu(II)-Catalyzed Enantioselective beta-Boration of beta-Trifluoromethyl, beta,beta-Disubstituted Enones and Esters: Construction of a CF3- and Boron-Containing Quaternary Stereocenter

Bing Liu et al.

ACS CATALYSIS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Copper-Catalyzed Asymmetric Defluoroborylation of 1-(Trifluoromethyl)Alkenes

Pan Gao et al.

CHEM (2018)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Asymmetric Borylation: Construction of a Stereogenic Carbon Center Bearing Both CF3 and Organoboron Functional Groups

Quanbin Jiang et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Mechanistic Studies of Copper-Catalyzed Asymmetric Hydroboration of Alkenes

Yumeng Xi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

The versatility of boron in biological target engagement

Diego B. Diaz et al.

NATURE CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereospecific functionalizations and transformations of secondary and tertiary boronic esters

Christopher Sandford et al.

CHEMICAL COMMUNICATIONS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Asymmetric Arylation/Defluorination of 1-(Trifluoromethyl)alkenes Forming Enantioenriched 1,1-Difluoroalkenes

Yinhua Huang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration

Yumeng Xi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

添加到收藏夹

Article Multidisciplinary Sciences

Catalytic, asymmetric difluorination of alkenes to generate difluoromethylated stereocenters

Steven M. Banik et al.

SCIENCE (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Michael Addition Catalyzed by Chiral Secondary Amine Phosphoramide Using Fluorinated Silyl Enol Ethers: Formation of Quaternary Carbon Stereocenters

Jin-Sheng Yu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Article Chemistry, Medicinal

Applications of Fluorine in Medicinal Chemistry

Eric P. Gillis et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

添加到收藏夹

Review Chemistry, Multidisciplinary

Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions

Xiaoyu Yang et al.

CHEMICAL REVIEWS (2015)

添加到收藏夹

Article Chemistry, Medicinal

Design and optimization of highly-selective fungal CYP51 inhibitors

William J. Hoekstra et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001-2011)

Jiang Wang et al.

CHEMICAL REVIEWS (2014)

添加到收藏夹

Article Chemistry, Medicinal

Repurposing the Antihistamine Terfenadine for Antimicrobial Activity against Staphylococcus aureus

Jessamyn I. Perlmutter et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantiospecific sp2-sp3 coupling of secondary and tertiary boronic esters

Amadeu Bonet et al.

NATURE CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Chiral Copper(II)-Catalyzed Enantioselective Boron Conjugate Additions to α,β-Unsaturated Carbonyl Compounds in Water

Shu Kobayashi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

添加到收藏夹

Review Chemistry, Multidisciplinary

Boron Containing Compounds as Protease Inhibitors

Reem Smoum et al.

CHEMICAL REVIEWS (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-Free Catalytic Enantioselective C-B Bond Formation: (Pinacolato)boron Conjugate Additions to α,β-Unsaturated Ketones, Esters, Weinreb Amides, and Aldehydes Promoted by Chiral N-Heterocyclic Carbenes

Hao Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

添加到收藏夹

Review Chemistry, Multidisciplinary

Asymmetric Construction of Stereogenic Carbon Centers Featuring a Trifluoromethyl Group from Prochiral Trifluoromethylated Substrates

Jing Nie et al.

CHEMICAL REVIEWS (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

An Efficient Copper(I)-Catalyst System for the Asymmetric Hydroboration of β-Substituted Vinylarenes with Pinacolborane

Dongwan Noh et al.

CHEMISTRY-AN ASIAN JOURNAL (2011)

添加到收藏夹

Review Chemistry, Multidisciplinary

Fluorine & chirality: how to create a nonracemic stereogenic carbon-fluorine centre?

Dominique Cahard et al.

CHEMICAL SOCIETY REVIEWS (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Amide-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes

Sean M. Smith et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Highly Regio- and Enantioselective Copper-Catalyzed Hydroboration of Styrenes

Dongwan Noh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

C-F Activation at Rhodium Boryl Complexes: Formation of 2-Fluoroalkyl-1,3,2-Dioxaborolanes by Catalytic Functionalization of Hexafluoropropene

Thomas Braun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Cross Coupling Reactions of Chiral Secondary Organoboronic Esters With Retention of Configuration

Daisuke Imao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

添加到收藏夹

Article Chemistry, Organic

Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents

Francis Beaulieu et al.

ORGANIC LETTERS (2009)

添加到收藏夹

Article Chemistry, Organic

Rediscovering Organocopper Chemistry Through Copper Hydride. It's All About the Ligand

Bruce H. Lipshutz

SYNLETT (2009)

添加到收藏夹

Review Chemistry, Multidisciplinary

CuH-catalyzed reactions

Carl Deutsch et al.

CHEMICAL REVIEWS (2008)

添加到收藏夹

Review Chemistry, Multidisciplinary

Update 1 of: Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions

Jun-An Ma et al.

CHEMICAL REVIEWS (2008)

添加到收藏夹

Review Chemistry, Multidisciplinary

Fluorine in medicinal chemistry

Sophie Purser et al.

CHEMICAL SOCIETY REVIEWS (2008)

添加到收藏夹

Editorial Material Chemistry, Medicinal

The many roles for fluorine in medicinal chemistry

William K. Hagmann

JOURNAL OF MEDICINAL CHEMISTRY (2008)

添加到收藏夹

Review Chemistry, Organic

Catalytic asymmetric hydroboration: Recent advances and applications in carbon-carbon bond-forming reactions

CM Crudden et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2003)

添加到收藏夹

Article Chemistry, Medicinal

Metabolism-directed optimization of 3-aminopyrazinone acetamide thrombin inhibitors. Development of an orally bioavailable series containing P1 and P3 pyridines

CS Burgey et al.

JOURNAL OF MEDICINAL CHEMISTRY (2003)

添加到收藏夹

Article Pharmacology & Pharmacy

New fluoroprostaglandin F-2 alpha derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents

T Nakajima et al.

BIOLOGICAL & PHARMACEUTICAL BULLETIN (2003)

添加到收藏夹

Article Chemistry, Organic

An exceptional hydroboration of substituted fluoroolefins providing tertiary alcohols

PV Ramachandran et al.

ORGANIC LETTERS (2001)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.