☆ 4.6 Article

A Versatile Route to Acyl (MIDA)Boronates

CHEMISTRY-A EUROPEAN JOURNAL (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

A Modular Access to 1,2-and 1,3-Disubstituted Cyclobut lboronic Esters by Consecutive Radical Additions

Jean Michalland et al.

Summary: A modular approach to substituted cyclobutylboronic esters is demonstrated, employing successive intermolecular radical additions. The stability of the alpha-boryl radical is tuned by the stabilizing influence of the trivalent boronic ester and the destabilizing cyclobutane, leading to the formation of a range of 1,2- and 1,3-disubstituted cyclobutylboronic esters. This method complements existing methods and offers a new avenue for obtaining these otherwise difficult-to-obtain compounds.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Preparation of Potassium Acyltrifluoroborates (KATs) from Carboxylic Acids by Copper-Catalyzed Borylation of Mixed Anhydrides**

Pinku Tung et al.

Summary: This method enables the easy preparation of various types of KATs and is compatible with a variety of functional groups, such as alkenes, esters, halides, nitriles, etc.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety

Andrej Sterman et al.

Summary: This work describes the preparation and application of primary trifluoroborate-iminiums (pTIMs) as a new and valuable class of organoboron derivatives. Highly enantioselective hydrogenation reactions were used to obtain chiral primary trifluoroborate-ammoniums (pTAMs). A facile conversion method using hexamethyldisiloxane/aqueous HCl was then used to synthesize diverse chiral alpha-aminoboronic acids from chiral pTAMs. The synthesis of optically pure anti-cancer drugs bortezomib and ixazomib demonstrated the practicality of this method.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Modular Access to 1,2-and 1,3-Disubstituted Cyclobutylboronic Esters by Consecutive Radical Additions

Jean Michalland et al.

Summary: This modular approach to substituted cyclobutylboronic esters involves successive intermolecular radical additions and reductive removal of xanthates to provide a range of 1,2- and 1,3-disubstituted cyclobutylboronic esters. The stability of the alpha-boryl radical is crucial for the success of the reaction, leveraging the stabilizing influence of the trivalent boronic ester and the slightly destabilizing cyclobutane. The chemistry described here complements existing methods by providing cyclobutylboronic esters that would be quite difficult to obtain otherwise.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Iridium-Catalysed C-H Borylation of Heteroarenes: Balancing Steric and Electronic Regiocontrol

Jay S. Wright et al.

Summary: The review focuses on the borylation of heteroarenes, with an emphasis on the influence of steric and electronic effects on regiochemical outcome. It is shown that the borylation of heterocyclic substrates is more challenging, with the position and nature of the heteroatoms significantly affecting the reactivity and regioselectivity of the reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

One-Step Synthesis of Acylboron Compounds via Copper-Catalyzed Carbonylative Borylation of Alkyl Halides**

Li-Jie Cheng et al.

Summary: A copper-catalyzed carbonylative borylation method has been developed for the synthesis of aliphatic potassium acyltrifluoroborates with high yields, tolerating a variety of functional groups and different alkyl halides. The mechanism involves a radical atom transfer carbonylation mechanism.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Medicinal

Targeting Metalloenzymes by Boron-Containing Metal-Binding Pharmacophores

You-Cai Xiao et al.

Summary: Metalloenzymes play critical roles in biological processes and are important therapeutic targets. This perspective focuses on the importance of exploiting metal-binding pharmacophores, specifically boron-containing MBPs, in inhibitor development targeting metalloenzymes. The challenges and design concepts regarding boron-containing MBPs are discussed, with emphasis on the unique binding modes with metalloenzyme active sites.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

A Convergent, Stereoselective Route to Trisubstituted Alkenyl Boronates

Jean Michalland et al.

Summary: A modular, stereoselective route to trisubstituted (Z)-alkenyl (MIDA)boronates was achieved by preparing vinyl boronate precursors through copper-catalyzed protoboration of propargyl alcohols, followed by radical addition-fragmentation of dithiocarbonates. This approach allowed for highly stereoselective fragmentation with the assistance of the bulky (MIDA)boronate.

ORGANIC LETTERS (2021)

添加到收藏夹

Review Chemistry, Multidisciplinary

Copper-Catalyzed Carbonylative Coupling of Alkyl Halides

Li-Jie Cheng et al.

Summary: Transition metal-catalyzed carbonylation reactions are an effective method to introduce oxygen functionality into organic compounds. However, challenges such as the use of noble metals as catalysts and the reactivity of certain substrates remain.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

添加到收藏夹

Article Chemistry, Medicinal

High-Throughput Crystallography Reveals Boron-Containing Inhibitors of a Penicillin-Binding Protein with Di- and Tricovalent Binding Modes

Hector Newman et al.

Summary: The research reveals that boron-containing compounds can form various complexes with PBP3, showing the potential for the development of new classes of boron-based antibiotics that are not affected by beta-lactamase-driven resistance.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Medicinal

Discovery of VNRX-7145 (VNRX-5236 Etzadroxil): An Orally Bioavailable β-Lactamase Inhibitor for Enterobacterales Expressing Ambler Class A, C, and D Enzymes

Robert E. Trout et al.

Summary: The production of beta-lactamase enzymes in Gram-negative bacteria causes antimicrobial resistance, leading to costly hospital visits and hospitalizations. A new compound, 5, has been developed to restore the activity of oral antibiotics against these difficult-to-treat bacteria.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Physical

C-H Borylation Catalysis of Heteroaromatics by a Rhenium Boryl Polyhydride

Liam J. Donnelly et al.

Summary: Transition metal complexes with metal-boron bonds, particularly iridium polyboryl and polyhydrido-boryl complexes, are important catalysts for C-H borylation reactions. In this study, polyhydride boryl phosphine rhenium complexes were shown to be capable of catalyzing the C-H borylation of heteroaromatic substrates. The boryl complex derived from the rhenium complex acted as a catalyst for various heteroarenes, exhibiting similar reactivity to iridium analogues.

ACS CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Physical

Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives

Luke Britton et al.

Summary: The manganese-catalyzed C-H borylation of furan and thiophene derivatives is reported along with an in situ activation method for accessing the active manganese hydride species. Mechanistic investigations showed that blue light irradiation directly affected catalysis by acting at the metal center, that C(sp(2))-H bond borylation occurs through a C-H metallation pathway, and that the reversible coordination of pinacolborane to the catalyst forms a manganese borohydride complex, which serves as an off-cycle resting state.

ACS CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

The modern role of boron as a 'magic element' in biomedical science: chemistry perspective

Saurav Chatterjee et al.

Summary: Boron was previously misunderstood as toxic to animals, hindering the development of boron-containing drugs, but with the WHO declaring boron as a 'probable essential element' for humans, the modern applications of boronic acid derivatives in biomedicine have become more attractive. The approval of five boronic acid-containing drugs by the FDA has greatly impacted the use of boron in various fields.

CHEMICAL COMMUNICATIONS (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Iron-Catalysed C(sp2)-H Borylation Enabled by Carboxylate Activation

Luke Britton et al.

MOLECULES (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Modular Synthesis of Furans with up to Four Different Substituents by a trans-Carboboration Strategy

Hongming Jin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Chemistry, Medicinal

Discovery of Cyclic Boronic Acid QPX7728, an Ultrabroad-Spectrum Inhibitor of Serine and Metallo-β-lactamases

Scott J. Hecker et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Synthesis of Acylboron Compounds

Dino Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent Advances in the Synthesis of Acylboranes and Their Widening Applicability

Andrej Sterman et al.

ACS OMEGA (2020)

添加到收藏夹

Article Chemistry, Organic

Synthesis of α-Bromoacetyl MIDA Boronate

C. Frank Lee et al.

ORGANIC SYNTHESES (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Concise Synthesis of Potassium Acyltrifluoroborates from Aldehydes through Copper(I)-Catalyzed Borylation/Oxidation

Jumpei Taguchi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Synthesis of Potassium Acyltrifluoroborates (KATs) through Chemoselective Cross-Coupling with a Bifunctional Reagent

Dino Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diversity-Oriented Synthesis of α-Functionalized Acylborons and Borylated Heteroarenes by Nucleophilic Ring Opening of α-Chloroepoxyboronates

Dong-Hang Tan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Radical Alliances: Solutions and Opportunities for Organic Synthesis

Samir Z. Zard

HELVETICA CHIMICA ACTA (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Carboxyboronate: A Versatile C1 Building Block

Aleksandra Holownia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons

Shengjia Lin et al.

CHEMICAL SCIENCE (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

The Xanthate Route to Ketones: When the Radical Is Better than the Enolate

Samir Z. Zard

ACCOUNTS OF CHEMICAL RESEARCH (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Boronic Acids as Bioorthogonal Probes for Site-Selective Labeling of Proteins

Burcin Akgun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

Melanie Trobe et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

添加到收藏夹

Review Chemistry, Applied

Current Applications of Suzuki-Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

Afsaneh Taheri Kal Koshvandi et al.

APPLIED ORGANOMETALLIC CHEMISTRY (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Thirty Years of (TMS)(3)SiH: A Milestone in Radical-Based Synthetic Chemistry

Chryssostomos Chatgilialoglu et al.

CHEMICAL REVIEWS (2018)

添加到收藏夹

Article Chemistry, Organic

One-Step Synthesis of Aliphatic Potassium Acyltrifluoroborates (KATs) from Organocuprates

Sizhou M. Liu et al.

ORGANIC LETTERS (2018)

添加到收藏夹

Article Chemistry, Organic

Synthesis of N,N-Alkylated α-Tertiary Amines by Coupling of α-Aminoalkyltrifluoroborates and Grignard Reagents

Moritz K. Jackl et al.

ORGANIC LETTERS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs)

Tomoya Shiro et al.

CHEMICAL SCIENCE (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Copper-boryl mediated organic synthesis

David Hemming et al.

CHEMICAL SOCIETY REVIEWS (2018)

添加到收藏夹

Article Chemistry, Organic

Preparation of 3,4-Substituted-5-Aminopyrazoles and 4-Substituted-2-Aminothiazoles

Stepan Havel et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

On the Strategic Impact of the Degenerative Transfer of Xanthates on Synthetic Planning

Beatrice Quiclet-Sire et al.

ISRAEL JOURNAL OF CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-Free Borylation of Heteroarenes Using Ambiphilic Aminoboranes: On the Importance of Sterics in Frustrated Lewis Pair C-H Bond Activation

Julien Legare Lavergne et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Review Chemistry, Organic

Acylboranes: synthetic strategies and applications

Florian Korbinian Scharnagl et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Recent Developments in Organoboron Chemistry: Old Dogs, New Tricks

James W. B. Fyfe et al.

CHEM (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct Access to MIDA Acylboronates through Mild Oxidation of MIDA Vinylboronates

Mathieu L. Lepage et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate

Jumpei Taguchi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Oxalyl Boronates Enable Modular Synthesis of Bioactive Imidazoles

C. Frank Lee et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Medicinal

Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?

Dean G. Brow et al.

JOURNAL OF MEDICINAL CHEMISTRY (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds

Diego B. Diaz et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Bifunctional Potassium Acyltrifluoroborates

Sizhou M. Liu et al.

ORGANIC LETTERS (2016)

添加到收藏夹

Review Chemistry, Multidisciplinary

Allylic Alcohols: Ideal Radical Allylating Agents?

Laurent Debien et al.

ACCOUNTS OF CHEMICAL RESEARCH (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Borylation using an Air-Stable Zinc Boryl Reagent: Systematic Access to Elusive Acylboranes

Jesus Campos et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Article Chemistry, Organic

Condensation-Driven Assembly of Boron-Containing Bis(Heteroaryl) Motifs Using a Linchpin Approach

Shinya Adachi et al.

ORGANIC LETTERS (2015)

添加到收藏夹

Article Multidisciplinary Sciences

Synthesis of many different types of organic small molecules using one automated process

Junqi Li et al.

SCIENCE (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Reagent for the One-Step Preparation of Potassium Acyltrifluoroborates (KATs) from Aryl- and Heteroarylhalides

Gabor Eros et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rapid Ligations with Equimolar Reactants in Water with the Potassium Acyltrifluoroborate (KAT) Amide Formation

Hidetoshi Noda et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans

Roohollah Kazem Shiroodi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines

Hidetoshi Noda et al.

CHEMICAL SCIENCE (2014)

添加到收藏夹

Article Chemistry, Multidisciplinary

Oxidative Geminal Functionalization of Organoboron Compounds

Zhi He et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Amide-Forming Ligation of Acyltrifluoroborates and Hydroxylamines in Water

Aaron M. Dumas et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Some Aspects of the Radical Chemistry of Xanthates

Beatrice Quiclet-Sire et al.

CHIMIA (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereospecific Cross-Coupling of Secondary Organotrifluoroborates: Potassium 1-(Benzyloxy)alkyltrifluoroborates

Gary A. Molander et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

添加到收藏夹

Article Chemistry, Organic

Synthesis of Acyltrifluoroborates

Aaron M. Dumas et al.

ORGANIC LETTERS (2012)

添加到收藏夹

Review Chemistry, Multidisciplinary

Natural and Synthetic Small Boron-Containing Molecules as Potential Inhibitors of Bacterial and Fungal Quorum Sensing

Valery M. Dembitsky et al.

CHEMICAL REVIEWS (2011)

添加到收藏夹

Article Chemistry, Organic

Modular Approach to Saturated and α,β-Unsaturated Ketones

Laurent Debien et al.

ORGANIC LETTERS (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Fun with radicals: Some new perspectives for organic synthesis

Beatrice Quiclet-Sire et al.

PURE AND APPLIED CHEMISTRY (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Generation and Reactions of an Unsubstituted N-Heterocyclic Carbene Boryl Anion

Julien Monot et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

添加到收藏夹

Article Chemistry, Organic

Synthesis of an Acyltrifluoroborate and Its Fusion with Azides To Form Amides

Gary A. Molander et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

添加到收藏夹

Article Chemistry, Organic

Recent progress in the synthesis of five-membered heterocycle boronic acids and esters

Nicolas Primas et al.

TETRAHEDRON (2010)

添加到收藏夹

Article Chemistry, Organic

Synthesis of potassium and tetra n-butylammonium 2-substituted-1,3-dithianotrifluoroborate salts and addition to chiral cyclic N-acyliminium ions

Adriano S. Vieira et al.

TETRAHEDRON (2008)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.