Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis
出版年份 2021 全文链接
标题
Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis
作者
关键词
-
出版物
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 36, Pages 14814-14826
出版商
American Chemical Society (ACS)
发表日期
2021-08-31
DOI
10.1021/jacs.1c06863
参考文献
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。- Application of C–H Functionalization in the Development of a Concise and Convergent Route to the Phosphatidylinositol-3-kinase Delta Inhibitor Nemiralisib
- (2021) Robert N. Bream et al. ORGANIC PROCESS RESEARCH & DEVELOPMENT
- Stopped‐Flow 19 F NMR Spectroscopic Analysis of a Protodeboronation Proceeding at the Sub‐Second Time‐Scale
- (2021) Ran Wei et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Sequential Ir/Cu-Mediated Method for the Meta-Selective C–H Radiofluorination of (Hetero)Arenes
- (2021) Jay S. Wright et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Rapid Estimation of T1 for Quantitative NMR
- (2021) Ran Wei et al. JOURNAL OF ORGANIC CHEMISTRY
- Equilibria in the 3-(trifluoromethyl)phenylboronic acid - boroxine system. Solubility of the acid and its cyclic esters in organic solvents
- (2021) Paweł Leszczyński et al. JOURNAL OF ORGANOMETALLIC CHEMISTRY
- Reactivity of Boronic Acids toward Catechols in Aqueous Solution
- (2020) Yota Suzuki et al. JOURNAL OF ORGANIC CHEMISTRY
- Arylboronic Acids and their Myriad of Applications Beyond Organic Synthesis
- (2020) Noemi de Jesus Hiller et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- The influence of ortho-substituents on the properties of phenylboronic acids
- (2020) Agnieszka Adamczyk-Woźniak et al. JOURNAL OF ORGANOMETALLIC CHEMISTRY
- Boronic Ester-Based Self-Healing Hydrogels Formed by Using Intermolecular B-N Coordination
- (2020) Yusheng Liu et al. POLYMER
- Design and discovery of boronic acid drugs
- (2020) Jessica Plescia et al. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
- Borylative Heterocyclization without Air-Free Techniques
- (2020) Chao Gao et al. JOURNAL OF ORGANIC CHEMISTRY
- Polyfluorinated arylboranes as catalysts in organic synthesis
- (2020) Nicolay Yu. Adonin et al. MENDELEEV COMMUNICATIONS
- Self-healing polymers
- (2020) Siyang Wang et al. Nature Reviews Materials
- The 2‐Pyridyl Problem: Challenging Nucleophiles in Cross‐Coupling Arylations
- (2020) Michael C. Willis et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- How Big is the Pinacol Boronic Ester as a Substituent?
- (2020) Valerio Fasano et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Photoinduced Borylation Reactions: An Overview
- (2020) B. Yadagiri et al. Asian Journal of Organic Chemistry
- Fluorinated Aryl Boronates as Building Blocks in Organic Synthesis
- (2020) Yudha Budiman et al. ADVANCED SYNTHESIS & CATALYSIS
- Improvement in the Palladium-Catalyzed Miyaura Borylation Reaction by Optimization of the Base: Scope and Mechanistic Study
- (2020) Santiago Barroso et al. JOURNAL OF ORGANIC CHEMISTRY
- Radiosynthesis of [ 18 F]ArylSCF 2 H Using Aryl Boronic Acids, S -(Chlorofluoromethyl)benzenesulfonothioate and [ 18 F]Fluoride
- (2020) Qunchao Zhao et al. CCS Chemistry
- In vivo Mutagenicity Testing of Arylboronic Acids and Esters
- (2019) Melisa J. Masuda‐Herrera et al. ENVIRONMENTAL AND MOLECULAR MUTAGENESIS
- Boronic acid‐functionalized agarose affinity chromatography for isolation of tropomyosin in fishes
- (2019) Jialuo Yin et al. JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
- Phenoxy-Dialkoxy Borates as a New Class of Readily Prepared Preactivated Reagents for Base-Free Cross-Coupling
- (2019) Marco Paladino et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- The mechanisms of boronate ester formation and fluorescent turn-on in ortho-aminomethylphenylboronic acids
- (2019) Xiaolong Sun et al. Nature Chemistry
- Boron in drug design: Recent advances in the development of new therapeutic agents
- (2019) Guilherme Felipe Santos Fernandes et al. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
- Kinetics and Mechanism of the Arase-Hoshi R2BH-Catalyzed Alkyne Hydroboration: Alkenylboronate Generation via B–H/C–B Metathesis
- (2019) Eduardo Nieto-Sepulveda et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Potassium Trimethylsilanolate Enables Rapid, Homogeneous Suzuki−Miyaura Cross-Coupling of Boronic Esters
- (2019) Connor P. Delaney et al. ACS Catalysis
- Elucidating the Role of the Boronic Esters in the Suzuki–Miyaura Reaction: Structural, Kinetic, and Computational Investigations
- (2018) Andy A. Thomas et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Synthesis of biologically active boron-containing compounds
- (2018) Fei Yang et al. MedChemComm
- An “On-Cycle” Precatalyst Enables Room-Temperature Polyfluoroarylation Using Sensitive Boronic Acids
- (2018) Liye Chen et al. ACS Catalysis
- Copper-boryl mediated organic synthesis
- (2018) David Hemming et al. CHEMICAL SOCIETY REVIEWS
- Self-Healing Boronic Acid-Based Hydrogels for 3D Co-cultures
- (2018) Megan E. Smithmyer et al. ACS Macro Letters
- Fluorinated Boronic Acids: Acidity and Hydrolytic Stability of Fluorinated Phenylboronic Acids
- (2017) Dorota Zarzeczańska et al. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
- Boron acid complexation reactions with polyols and α-hydroxy carboxylic acids: Equilibria, reaction mechanisms, saccharide recognition
- (2017) Richard Pizer INORGANICA CHIMICA ACTA
- Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates
- (2017) David Bulfield et al. JOURNAL OF ORGANIC CHEMISTRY
- Triple responsive block copolymers combining pH-responsive, thermoresponsive, and glucose-responsive behaviors
- (2017) William L. A. Brooks et al. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
- Spectroscopic Studies of the Chan–Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity
- (2017) Julien C. Vantourout et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion
- (2017) Paul A. Cox et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study
- (2017) Thomas H. West et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Doubly Dynamic Self-Healing Materials Based on Oxime Click Chemistry and Boronic Acids
- (2017) Joe Collins et al. MACROMOLECULAR RAPID COMMUNICATIONS
- The versatility of boron in biological target engagement
- (2017) Diego B. Diaz et al. Nature Chemistry
- Recent Developments in Organoboron Chemistry: Old Dogs, New Tricks
- (2017) James W.B. Fyfe et al. Chem
- Borate esters: Simple catalysts for the sustainable synthesis of complex amides
- (2017) Marco T. Sabatini et al. Science Advances
- Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates
- (2016) Kyan A. D’Angelo et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Protodeboronation of Heteroaromatic, Vinyl, and Cyclopropyl Boronic Acids: pH–Rate Profiles, Autocatalysis, and Disproportionation
- (2016) Paul A. Cox et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- MIDA boronates are hydrolysed fast and slow by two different mechanisms
- (2016) Jorge A. Gonzalez et al. Nature Chemistry
- Synthesis and polymerization of boronic acid containing monomers
- (2016) Gertjan Vancoillie et al. Polymer Chemistry
- Responsive Boronic Acid-Decorated (Co)polymers: From Glucose Sensors to Autonomous Drug Delivery
- (2016) Gertjan Vancoillie et al. SENSORS
- A Surprising Substituent Effect Provides a Superior Boronic Acid Catalyst for Mild and Metal-Free Direct Friedel-Crafts Alkylations and Prenylations of Neutral Arenes
- (2015) Carolynne L. Ricardo et al. CHEMISTRY-A EUROPEAN JOURNAL
- Harnessing C–H Borylation/Deborylation for Selective Deuteration, Synthesis of Boronate Esters, and Late Stage Functionalization
- (2015) Venkata A Kallepalli et al. JOURNAL OF ORGANIC CHEMISTRY
- Organotrifluoroborates: Another Branch of the Mighty Oak
- (2015) Gary A. Molander JOURNAL OF ORGANIC CHEMISTRY
- A modular synthesis of functionalised phenols enabled by controlled boron speciation
- (2015) John J. Molloy et al. ORGANIC & BIOMOLECULAR CHEMISTRY
- Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids
- (2015) Andrew V. Mossine et al. ORGANIC LETTERS
- A synthesis of abemaciclib utilizing a Leuckart–Wallach reaction
- (2015) Michael O. Frederick et al. TETRAHEDRON LETTERS
- Lithiation–Borylation Methodology and Its Application in Synthesis
- (2014) Daniele Leonori et al. ACCOUNTS OF CHEMICAL RESEARCH
- Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes
- (2014) Orit Jacobson et al. BIOCONJUGATE CHEMISTRY
- Universal Reaction Mechanism of Boronic Acids with Diols in Aqueous Solution: Kinetics and the Basic Concept of a Conditional Formation Constant
- (2014) Yuki Furikado et al. CHEMISTRY-A EUROPEAN JOURNAL
- Interactions between boric acid derivatives and saccharides in aqueous media: Structures and stabilities of resulting esters
- (2014) Joop A. Peters COORDINATION CHEMISTRY REVIEWS
- Base-Promoted Protodeboronation of 2,6-Disubstituted Arylboronic Acids
- (2014) Jerome Lozada et al. JOURNAL OF ORGANIC CHEMISTRY
- Selectivity and Isotope Effects in Hydronation of a Naked Aryl Anion
- (2014) Charles L. Perrin et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Iridium-Catalyzed C–H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism
- (2014) Matthew A. Larsen et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Synthesis of hydroxyphthioceranic acid using a traceless lithiation–borylation–protodeboronation strategy
- (2014) Ramesh Rasappan et al. Nature Chemistry
- Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011)
- (2013) Jiang Wang et al. CHEMICAL REVIEWS
- Selective sensing of saccharides using simple boronic acids and their aggregates
- (2013) Xin Wu et al. CHEMICAL SOCIETY REVIEWS
- Selection of boron reagents for Suzuki–Miyaura coupling
- (2013) Alastair J. J. Lennox et al. CHEMICAL SOCIETY REVIEWS
- Protodeboronation of ortho- and para-Phenol Boronic Acids and Application to ortho and meta Functionalization of Phenols Using Boronic Acids as Blocking and Directing Groups
- (2013) Chun-Young Lee et al. JOURNAL OF ORGANIC CHEMISTRY
- Organoboron Acids and Their Derivatives as Catalysts for Organic Synthesis
- (2013) Elena Dimitrijević et al. ACS Catalysis
- A decade advancement of transition metal-catalyzed borylation of aryl halides and sulfonates
- (2013) Wing Kin Chow et al. RSC Advances
- Exploiting the Reversible Covalent Bonding of Boronic Acids: Recognition, Sensing, and Assembly
- (2012) Steven D Bull et al. ACCOUNTS OF CHEMICAL RESEARCH
- Supramolecular Binding Thermodynamics by Dispersion-Corrected Density Functional Theory
- (2012) Stefan Grimme CHEMISTRY-A EUROPEAN JOURNAL
- A C–H Borylation Approach to Suzuki–Miyaura Coupling of Typically Unstable 2–Heteroaryl and Polyfluorophenyl Boronates
- (2012) Daniel W. Robbins et al. ORGANIC LETTERS
- Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels–Alder cycloaddition
- (2012) Hongchao Zheng et al. TETRAHEDRON LETTERS
- Susceptibility to hydrolysis of phenylboronic pinacol esters at physiological pH
- (2012) Cesare Achilli et al. Open Chemistry
- Borylation and Silylation of C–H Bonds: A Platform for Diverse C–H Bond Functionalizations
- (2011) John F. Hartwig ACCOUNTS OF CHEMICAL RESEARCH
- Regioselectivity of the borylation of alkanes and arenes
- (2011) John F. Hartwig CHEMICAL SOCIETY REVIEWS
- Aryl Trihydroxyborate Salts: Thermally Unstable Species with Unusual Gelation Abilities
- (2011) Cheryl L. Moy et al. JOURNAL OF ORGANIC CHEMISTRY
- Arylboronic acids: A diabetic eye on glucose sensing
- (2011) Jon Stefan Hansen et al. SENSORS AND ACTUATORS B-CHEMICAL
- Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride
- (2010) Mike Butters et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- The thermal and boron-catalysed direct amide formation reactions: mechanistically understudied yet important processes
- (2010) Hayley Charville et al. CHEMICAL COMMUNICATIONS
- Boronic Acid Catalysis for Mild and Selective [3+2] Dipolar Cycloadditions to Unsaturated Carboxylic Acids
- (2010) Hongchao Zheng et al. CHEMISTRY-A EUROPEAN JOURNAL
- The Slow-Release Strategy in Suzuki-Miyaura Coupling
- (2010) Alastair J. J. Lennox et al. ISRAEL JOURNAL OF CHEMISTRY
- Differentially Protected Diboron for Regioselective Diboration of Alkynes: Internal-Selective Cross-Coupling of 1-Alkene-1,2-diboronic Acid Derivatives
- (2010) Noriyuki Iwadate et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Direct C−H Arylation of Electron-Deficient Heterocycles with Arylboronic Acids
- (2010) Ian B. Seiple et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- A New Palladium Precatalyst Allows for the Fast Suzuki−Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids
- (2010) Tom Kinzel et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Mild and efficient boronic acid catalysis of Diels–Alder cycloadditions to 2-alkynoic acids
- (2010) Hongchao Zheng et al. TETRAHEDRON LETTERS
- Boronic acids in medicinal chemistry: anticancer, antibacterial and antiviral applications
- (2010) Paul C. Trippier et al. MedChemComm
- C−H Activation for the Construction of C−B Bonds
- (2009) Ibraheem A. I. Mkhalid et al. CHEMICAL REVIEWS
- Easily Attachable and Detachableortho-Directing Agent for Arylboronic Acids in Ruthenium-Catalyzed Aromatic C−H Silylation
- (2009) Hideki Ihara et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Density Functionals with Broad Applicability in Chemistry
- (2008) Yan Zhao et al. ACCOUNTS OF CHEMICAL RESEARCH
- Direct and Waste-Free Amidations and Cycloadditions by Organocatalytic Activation of Carboxylic Acids at Room Temperature
- (2008) Raed M. Al-Zoubi et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Kinetic Evidence for High Reactivity of 3-Nitrophenylboronic Acid Compared to Its Conjugate Boronate Ion in Reactions with Ethylene and Propylene Glycols
- (2008) Chiaki Miyamoto et al. INORGANIC CHEMISTRY
Find the ideal target journal for your manuscript
Explore over 38,000 international journals covering a vast array of academic fields.
SearchBecome a Peeref-certified reviewer
The Peeref Institute provides free reviewer training that teaches the core competencies of the academic peer review process.
Get Started