☆ 4.6 Review

Transition Metal-Free Aromatic C-H, C-N, C-S and C-O Borylation

CHEMICAL RECORD (2023)

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Article Chemistry, Multidisciplinary

Electrochemical borylation of nitroarenes

Linlin Du et al.

Summary: A simple electrochemically mediated method for converting nitroarenes to aryl boronic esters is described. This method enables the electrochemical borylation of a wide range of nitroarenes, including late-stage borylation of bioactive molecules, under simple conditions at room temperature, demonstrating its broad applicability and functional group tolerance. The transformation provides a convenient and practical access to aryl boronic esters from readily available nitroarenes, streamlining the synthetic process of diverse functionalized arenes.

SCIENCE CHINA-CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Visible Light-Induced C-5 Selective C-H Radical Borylation of Imidazo[1,2-a]pyridines with NHC-Boranes

Huitao Zheng et al.

Summary: In this study, a visible-light-induced C-5 selective C-H borylation method of imidazo[1,2-a]pyridines via Minisci-type radical borylation reaction was successfully developed for the first time. This sustainable protocol provides a new approach to prepare regioselectively C5-borylated imidazopyridines, which would otherwise be challenging to synthesize, and serves as a supplement to the site-selective borylation of azines and the assembly of sp(2) carbon-boron bond.

CHINESE JOURNAL OF CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Metal-Free Phosphorus-Directed Borylation of C(sp2)-H Bonds

Omar Sadek et al.

Summary: A new method has been developed for the synthesis of phosphine-boranes, featuring simplicity, efficiency, and broad substrate scope. The key intermediates were identified as P-stabilized borenium cations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Multidisciplinary

Photochemical and electrochemical C-N borylation of arylhydrazines

Linlin Du et al.

Summary: The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was successfully achieved using photochemical and electrochemical conditions, providing two efficient and mild transition-metal-free synthetic routes towards aryl boronate esters from readily available arylhydrazines.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

BBr3-Mediated P(III)-Directed C-H Borylation of Phosphines

Jiahang Lv et al.

Summary: The study developed a metal-free P(III)-directed phosphine C-H borylation method, mediated by BBr3, to synthesize products containing both phosphorus and boron. The metal-free strategy features low cost, practicality, and environmental friendliness.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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Article Chemistry, Organic

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Shuohan Ji et al.

Summary: In this study, unreactive C-N bonds in anilines were successfully activated through photoinduced aerobic borylation, leading to the conversion of a variety of tertiary and secondary anilines to aryl boronate esters in moderate to good yields with wide functional group tolerance. This transformation provides a direct and convenient route for converting readily available anilines into useful aryl boronate esters.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Metal-free directed C-H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines

Gaorong Wu et al.

Summary: This study reports a novel metal-free method for C-H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines. The reaction exhibited high efficiency and site exclusivity, allowing for gram-scale synthesis of borylated products with good derivatization applications. Furthermore, the directing group could be easily removed.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Metal-Free Boron-Mediated ortho-C-H Hydroxylation of N-Benzyl-3,4,5-tribromopyrazoles

Gaorong Wu et al.

Summary: A novel method for C-H hydroxylation of benzyl compounds directed by a 3,4,5-tribromopyrazole auxiliary via boronation/oxidation has been reported. The strategy shows outstanding site selectivity and yields the corresponding phenols in moderate to excellent yields under metal-free conditions.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Mild, Organo-Catalysed Borono-Deamination as a Key to Late-Stage Pharmaceutical Precursors and 18F-Labelled Radiotracers

Raul M. Perez-Garcia et al.

Summary: A tris(pentafluorophenyl)borane catalysed method for the synthesis of boronic acid esters from aromatic amines with high yields was developed. The method features mild conditions, benign reagents, short reaction times, low temperatures, and a wide substrate scope, making it suitable for the synthesis of boronic acid ester derivatives of complex drug molecules.

FRONTIERS IN CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Borenium-Ion-Catalyzed C-H Borylation of Arenes

Xinyue Tan et al.

Summary: This study presents the development of a metal-free catalyst for the borylation of unactivated arenes. The catalyst enables the borylation of sterically encumbered positions and achieves para-selective borylation of phenols, both of which are challenging tasks for transition-metal systems. Mechanistic studies support a synergistic activation mechanism involving the catalyst and the borylation reagent.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Borylation Directed Borylation of Indoles Using Pyrazabole Electrophiles: A One-Pot Route to C7-Borylated-Indolines

Jurgen Pahl et al.

Summary: In this research, a new diboron compound, Pyrazabole (1), was discovered, which can be transformed into ditopic electrophiles. The unique B center dot center dot center dot B separation in 1 enables double E-H functionalization of indoles and indolines. Specifically, the activation of 1 with HNTf2 generates an electrophile that can convert N-H indoles and indolines into N/C7-diborylated indolines.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

Regioselective Transition-Metal-Free C(sp2)-H Borylation: A Subject of Practical and Ongoing Interest in Synthetic Organic Chemistry

Supriya Rej et al.

Summary: Considerable advances have been made in the field of C-H functionalization, with special interest in C-H borylation due to its wide applications. Transition-metal-catalyzed regioselective strategies have been developed, but the use of precious metals and contamination by metal precursors limit their application in large-scale synthesis. Recent trends involve the use of transition-metal-free systems.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Organic

C4-Selective C-H Borylation of Pyridinium Derivatives Driven by Electron Donor-Acceptor Complexes

Wonjun Choi et al.

Summary: The photoinduced C4-selective C-H borylation of pyridines was achieved using electron donor-acceptor complexes derived from a Lewis base and N-amidopyridinium salts under external oxidant-and photocatalyst-free conditions. This approach provides a versatile platform for the installation of both phosphite-and amine-coordinated boron groups on a series of pyridines under mild conditions, demonstrating excellent C4-positional selectivity for the pyridine scaffolds.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Direct photolysis of N-methoxypyridiniums for the pyridylation of carbon/heteroatom-hydrogen bonds

He Sheng et al.

Summary: Current methods for synthesizing pyridinium salts often require transition metals, oxidants, and/or photocatalysts. This paper presents the first direct photolysis method for N-methoxypyridinium salts without the need for photocatalysts, transition metals, or oxidants. Common feedstocks such as amine-boranes, unactivated alkanes, phosphine oxides, amides, silanes, and aldehydes can be selectively assembled into various pyridines using this method.

SCIENCE CHINA-CHEMISTRY (2022)

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Article Chemistry, Organic

Photoinduced Divergent Deaminative Borylation and Hydrodeamination of Primary Aromatic Amines

Akira Shiozuka et al.

Summary: This study developed a divergent deaminative borylation and hydrodeamination of primary aromatic amines using bis(pinacolato)diboron. These transformations can be switched by the reaction conditions. Mechanistic and computational studies suggested that the cleavage of the C-N bond and the formation of C-B bond do not involve free aryl radical intermediates, but hydrodeamination proceeds via hydrogen atom transfer between the corresponding aryl radical and an ethereal solvent.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Adamantane-1-Carbonyl-Directed C-H Borylation and Hydroxylation of Benzenethiols

Xiaobo Xu et al.

Summary: A novel route for C-H borylation and hydroxylation of benzenethiols directed by adamantane-1carbonyl using BBr3 has been described. The protocol allows for the generation of corresponding arylboronic esters and phenols in moderate to excellent yields under metal-free conditions. Additionally, the borylated product can be transformed and the directing group can be removed in good yields, facilitating the synthesis of structurally diverse benzenethiols.

ORGANIC LETTERS (2022)

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Article Chemistry, Multidisciplinary

Photoinduced Dehydrogenative Borylation via Dihydrogen Bond Bridged Electron Donor and Acceptor Complexes

Zhiyong Wang et al.

Summary: Air-stable amine- and phosphine-boranes have been discovered as donors to form photoactive electron-donor-acceptor (EDA) complexes with pyridinium acceptor. The EDA complex, upon irradiation, undergoes intra-complex single electron transfer without the need for external photosensitizer and radical initiator, leading to the formation of a boron-centered radical for dehydrogenative borylation. DFT calculations suggest that the deprotonation of the Wheland-like radical intermediate, rather than its generation, determines the good ortho-selectivity. Various alpha-borylated pyridine derivatives can be easily synthesized with good functional group tolerance.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

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Review Chemistry, Multidisciplinary

Metal-catalysed C-H bond activation and borylation

Ranjana Bisht et al.

Summary: Transition metal-catalysed direct borylation of hydrocarbons via C-H bond activation has gained significant attention for its synthetic versatility. Selectivity control is a challenging issue, but recent efforts have led to impressive progress in both proximal and distal C-H bond borylation reactions. Innovative methodologies have been developed for ortho C-H bond borylation reactions, while meta and para selective reactions remain a challenge. Advancements have also been made for aliphatic C(sp(3))-H borylations and enantioselective borylations. This review discusses the development of different approaches and findings since 2014, as well as various applications of C-H borylation reactions in the synthesis of natural products, therapeutics, and materials chemistry.

CHEMICAL SOCIETY REVIEWS (2022)

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Article Chemistry, Organic

Photoinduced aerobic C-S borylation of aryl sulfides

Xinqi Li et al.

Summary: Direct C-S borylation of aryl sulfides with B(2)pin(2) has been achieved through a transition-metal-free photochemical process under blue LED irradiation, using 1,4-benzoquinone as the photosensitizer. This transformation offers a new opportunity for the conversion of alkylthio group, which is widely present, into a convertible group for organic synthesis.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Review Chemistry, Multidisciplinary

Recent advances in borenium catalysis

Xinyue Tan et al.

Summary: This review provides an overview of recent advancements in borenium-catalyzed reactions, with a focus on catalyst synthesis, methodology development, and mechanistic insight.

CHEMICAL SOCIETY REVIEWS (2022)

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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)

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Article Chemistry, Multidisciplinary

Metal-Free Directed C-H Borylation of Pyrroles

Zheng-Jun Wang et al.

Summary: The research presents a general strategy for site-selective C-H borylation of pyrroles using BBr3 directed by pivaloyl groups, without the need for any metal catalysts. The reaction is influenced by chelation and electronic effects, leading to diverse products with high positional selectivity and downstream transformation capabilities. DFT calculations confirm the preferred positional selectivity of this reaction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Applied

Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2

Rongkang Wang et al.

Summary: An efficient electrochemical synthesis method has been developed for the production of various unsymmetrical thioethers and arylboronates. This approach utilizes stable arylazo sulfones as radical precursors for carbon-heteroatom bond formation under electrochemical conditions, and shows scalability for gram-scale reactions. The protocol avoids the use of stoichiometric oxidants, metal catalysts, activating agents, and added bases, while also demonstrating favorable functional group tolerance.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Review Chemistry, Multidisciplinary

Photoinduced Borylation for the Synthesis of Organoboron Compounds Focus Review

Ya-Ming Tian et al.

Summary: This review summarizes the research on photoinduced borylations, focusing on recent developments and trends. Studies cover the catalytic methods, substrates, and reaction mechanisms of boronations.

CHEMICAL REVIEWS (2021)

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Review Chemistry, Inorganic & Nuclear

Recent advances in transition-metal-mediated Csp2-B and Csp2-P cross-coupling reactions

Laxmidhar Rout et al.

Summary: Arylboron and arylphosphorus compounds are important structures in synthetic chemistry for constructing complex molecules. Transition-metal-mediated C-B and C-P cross-couplings are powerful tools for synthesizing these compounds, allowing for the functionalization of reactive aryl halides. Efforts have been made to expand the scope of these reactions to include carboxylic acid derivatives and the functionalization of C-F and C-H bonds.

COORDINATION CHEMISTRY REVIEWS (2021)

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Article Chemistry, Organic

Construction of 1,2,3-Benzodiazaborole by Electrophilic Borylation of Azobenzene and Nucleophilic Dialkylative Cyclization

Masanori Shigeno et al.

Summary: The study presents a convenient method for the preparation of 1,2,3-benzodiazaboroles from azobenzenes, involving electrophilic ortho-borylation and dialkylative cyclization to introduce different substituents and Grignard reagents, showcasing novel reaction mechanisms and aromatic properties.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Transient Imine as a Directing Group for the Metal-Free o-C-H Borylation of Benzaldehydes

Supriya Rej et al.

Summary: Organoboron reagents play a crucial role in synthetic organic chemistry, and current selective borylation strategies rely heavily on transition-metal catalysts. However, this study introduces a transition-metal-free approach for selective C-H borylation of electron-deficient benzaldehyde derivatives, demonstrating effectiveness even in the presence of external impurities.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Organic

Metal-Free ortho-Selective C-H Borylation of 2-Phenylthiopyridines Using BBr3

Gaorong Wu et al.

Summary: A novel method for the ortho-selective C-H borylation of 2-phenylthiopyridines using BBr3 as the boron source under metal-free conditions has been reported. The reaction shows site exclusivity, and the synthesized aryl boronates can be readily converted into various useful intermediates. This facile method is advantageous for synthesizing structurally diversified phenylthioethers derivatives and other materials containing boron-nitrogen coordination.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Benzoic Acid-Promoted C2-H Borylation of Indoles with Pinacolborane

Youliang Zou et al.

Summary: A benzoic acid-promoted C2-H borylation of indoles with pinacolborane is developed, providing a prompt route toward the synthesis of diverse C2-functionalized indoles. Preliminary mechanistic studies suggest that BH3-related borane species formed via the decomposition of pinacolborane may be the probable catalyst.

ORGANIC LETTERS (2021)

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Article Multidisciplinary Sciences

A radical approach for the selective C-H borylation of azines

Ji Hye Kim et al.

Summary: A new strategy for the borylation of azines has been developed, utilizing stable and inexpensive amine-borane reagents in conjunction with photocatalysis. This approach allows for selective borylation of nitrogen-containing aromatic heterocycles through the formation of highly reactive boryl radicals, providing an alternative tactic for sp(2) carbon-boron bond assembly. The strong nucleophilic character of the amine-boryl radicals enables predictable and site-selective carbon-boron bond formation in azine structures, leading to the preparation of borylated materials that are otherwise difficult to access.

NATURE (2021)

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Article Chemistry, Organic

Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2

Akira Shiozuka et al.

Summary: Direct unreactive C-N borylation of aromatic amines was achieved using a photocatalyst, with improved yield of borylated products under a CO2 atmosphere, suggesting a possible mechanism involving C-N bond cleavage and C-B bond formation via a concerted pathway.

ORGANIC LETTERS (2021)

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Review Chemistry, Organic

Boron Lewis Pair Mediated C-H Activation and Borylation

Frederic-Georges Fontaine et al.

Summary: In recent years, the chemistry of frustrated Lewis pairs (FLP) has enabled various transformations, particularly in C-H bond activation and borylation reactions. A comparison is made between FLP borylation chemistry and early borylation methodologies. The mechanism of C-H borylation using inter- and intramolecular Lewis pairs, along with some applications, is presented.

SYNTHESIS-STUTTGART (2021)

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Article Chemistry, Multidisciplinary

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Shun Wang et al.

Summary: Efforts are being made to develop photo-redox catalysts with high redox power, although current methods face challenges in activating bonds with high bond dissociation energy and substrates with high reduction potentials. A novel photocatalytic strategy using thiolate as a catalyst has been introduced for the activation of inert substituted arenes for aryl borylation, expanding the scope of aryl radical precursors and demonstrating good functional-group tolerance. Spectroscopic investigations suggest the formation of a charge-transfer complex as the key step to activate the substrates.

CHEM (2021)

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Article Chemistry, Multidisciplinary

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Li Wang et al.

Summary: Selective carbon-carbon bond activation was achieved through fragmentation borylation mediated by B(OMe)(3)/B(2)pin(2), leading to the formation of two C-B bonds in non-polar unstrained Csp(2)-Csp(3) and Csp(2)-Csp(2) bonds. This new reaction mode is expected to stimulate the development of reactions based on inert C-C bond activation, as suggested by preliminary mechanistic investigations.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Multidisciplinary

Pyrimidine-directed metal-free C-H borylation of 2-pyrimidylanilines: a useful process for tetra-coordinated triarylborane synthesis

Supriya Rej et al.

Summary: This study presents a metal-free directed ortho-C-H borylation of 2-pyrimidylaniline derivatives, leading to the synthesis of various boronates and triarylborane derivatives. The reaction proceeds smoothly without interference by external impurities, highlighting its importance in synthetic chemistry.

CHEMICAL SCIENCE (2021)

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Article Chemistry, Organic

Radical generation from electroreduction of aryl and benzyl ammonium salts: synthesis of organoboronates

Xianqiang Kong et al.

Summary: This study presents a direct electrocatalytic borylation reaction at room temperature, which is compatible with substrates bearing various functional groups and does not require stoichiometric metals, external reducing agents, or sacrificial anodes. The protocol shows great potential for gram-scale synthesis.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Para-selective borylation of monosubstituted benzenes using a transient mediator

Jie Wu et al.

SCIENCE CHINA-CHEMISTRY (2020)

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Direct C-H Bond Borylation of (Hetero)Arenes: Evolution from Noble Metal to Metal Free

Yahui Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Radical C-N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent

Yuanhong Ma et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Article Chemistry, Multidisciplinary

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Shengfei Jin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Multiple Electrophilic C-H Borylation of Arenes Using Boron Triiodide

Susumu Oda et al.

ORGANIC LETTERS (2020)

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Methodologies and Strategies for Selective Borylation of C-Het and C-C Bonds

Minyan Wang et al.

CHEMICAL REVIEWS (2020)

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Metal-Free C-H Borylation of N-Heteroarenes by Boron Trifluoride

Vladimir Iashin et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Metal-Free Catalytic Aromatic C-H Borylation

Hua Zhang et al.

SYNLETT (2020)

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Article Chemistry, Organic

C-H Borylation of Diphenylamines through Adamantane-1-carbonyl Auxiliary by BBr3

Gaorong Wu et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Multidisciplinary

Intramolecular (directed) electrophilic C-H borylation

S. A. Iqbal et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Article Biochemistry & Molecular Biology

Direct Transformation from Arylamines to Aryl Naphthalene-1,8-diamino Boronamides: A Metal-Free Sandmeyer-Type Process

Siyi Ding et al.

MOLECULES (2019)

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Article Chemistry, Organic

Visible Light-Promoted Formation of C-B and C-S Bonds under Metal- and Photocatalyst-Free Conditions

Lena Blank et al.

SYNTHESIS-STUTTGART (2019)

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Article Chemistry, Multidisciplinary

Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis

Etienne Rochette et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Metal-free directed sp2-C-H borylation

Jiahang Lv et al.

NATURE (2019)

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Article Chemistry, Multidisciplinary

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Saqib A. Iqbal et al.

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Review Chemistry, Medicinal

Boron in drug design: Recent advances in the development of new therapeutic agents

Guilherme Felipe Santos Fernandes et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2019)

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Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light

Chen Huang et al.

ORGANIC LETTERS (2019)

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Soren K. Mellerup et al.

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B(C6F5)(3)-Catalyzed C3-Selective C-H Borylation of Indoles: Synthesis, Intermediates, and Reaction Mechanism

Sutao Zhang et al.

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The electrophilic aromatic substitution approach to C-H silylation and C-H borylation

Susanne Baehr et al.

PURE AND APPLIED CHEMISTRY (2018)

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Boron(III)-Catalyzed C2-Selective C-H Borylation of Heteroarenes

Qi Zhong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Selective C-N Borylation of Alkyl Amines Promoted by Lewis Base

Jiefeng Hu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Organic

Additive- and Photocatalyst-Free Borylation of Arylazo Sulfones under Visible Light

Yuliang Xu et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Photoinduced Deaminative Borylation of Alkylamines

Jingjing Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Four-coordinate triarylborane synthesis via cascade B-Cl/C-B cross-metathesis and C-H bond borylation

Kai Yang et al.

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Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor-Acceptor Complex

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Practical and Scalable Synthesis of Borylated Heterocycles Using Bench-Stable Precursors of Metal-Free Lewis Pair Catalysts

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CATALYTIC AROMATIC BORYLATION VIA IN SITU-GENERATED BORENIUM SPECIES

Fumiya Kitani et al.

HETEROCYCLES (2017)

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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.

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Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature

Wenbo Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

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The versatility of boron in biological target engagement

Diego B. Diaz et al.

NATURE CHEMISTRY (2017)

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Review Chemistry, Organic

Formal nucleophilic borylation and borylative cyclization of organic halides

K. Kubota et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Article Chemistry, Organic

Recent advances in catalytic C-H borylation reactions

Liang Xu et al.

TETRAHEDRON (2017)

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Article Chemistry, Organic

Borylation of aryldiazonium salts at room temperature in an aqueous solution under catalyst-free conditions

Xinxin Qi et al.

TETRAHEDRON LETTERS (2017)

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Article Chemistry, Multidisciplinary

Recent developments in and perspectives on three-coordinate boron materials: a bright future

Lei Ji et al.

CHEMICAL SCIENCE (2017)

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Article Chemistry, Multidisciplinary

Metal-Free Arene and Heteroarene Borylation Catalyzed by Strongly Electrophilic Bis-boranes

Yun-Lin Liu et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Article Chemistry, Multidisciplinary

Catalytic Electrophilic C-H Borylation Using NHC•Boranes and Iodine Forms C2-, not C3-, Borylated Indoles

John S. McGough et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

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Article Chemistry, Multidisciplinary

Catalytic Friedel-Crafts C-H Borylation of Electron-Rich Arenes: Dramatic Rate Acceleration by Added Alkenes

Qin Yin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

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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)

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Article Chemistry, Multidisciplinary

Atom-Efficient Synthesis of Alkynylfluoroborates Using BF3-Based Frustrated Lewis Pairs

Vladimir Iashin et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Article Chemistry, Multidisciplinary

Metal-Free sp2-C-H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes

Konstantin Chernichenko et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Chemistry, Multidisciplinary

Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts

Adelphe M. Mfuh et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Article Chemistry, Organic

One-pot Suzuki coupling of aromatic amines via visible light photocatalyzed metal free borylation using t-BuONO at room temperature

Sabir Ahammed et al.

TETRAHEDRON LETTERS (2016)

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Article Chemistry, Organic

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

George Iakobson et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2015)

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Article Chemistry, Multidisciplinary

Regioselective electrophilic borylation of haloarenes

Alessandro Del Grosso et al.

CHEMICAL COMMUNICATIONS (2015)

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Article Multidisciplinary Sciences

Metal-free catalytic C-H bond activation and borylation of heteroarenes

Marc-Andre Legare et al.

SCIENCE (2015)

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Article Chemistry, Organic

Sequential One-Pot Access to Molecular Diversity through Aniline Aqueous Borylation

William Erb et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

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Article Chemistry, Organic

Regioselective Synthesis of Substituted Tetrahydrofurans through Prins Cyclization

Li-Ming Zhao et al.

SYNLETT (2014)

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Article Chemistry, Organic

Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation

Di Qiu et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

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Article Chemistry, Multidisciplinary

Mechanistic Studies into Amine-Mediated Electrophilic Arene Borylation and Its Application in MIDA Boronate Synthesis

Viktor Bagutski et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Article Chemistry, Multidisciplinary

Catalytic Generation of Borenium Ions by Cooperative B-H Bond Activation: The Elusive Direct Electrophilic Borylation of Nitrogen Heterocycles with Pinacolborane

Timo Stahl et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

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Article Chemistry, Organic

P-Directed Borylation of Phenols

Clement Cazorla et al.

ORGANIC LETTERS (2013)

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Review Chemistry, Multidisciplinary

A decade advancement of transition metal-catalyzed borylation of aryl halides and sulfonates

Wing Kin Chow et al.

RSC ADVANCES (2013)

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Article Chemistry, Applied

Metal-Free, Visible Light-Induced Borylation of Aryldiazonium Salts: A Simple and Green Synthetic Route to Arylboronates

Jian Yu et al.

ADVANCED SYNTHESIS & CATALYSIS (2012)

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Article Chemistry, Organic

Metal-Free Ortho C-H Borylation of 2-Phenoxypyridines under Mild Conditions

Liting Niu et al.

ORGANIC LETTERS (2012)

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Article Chemistry, Organic

Transition-Metal-Free Borylation of Aryltriazene Mediated by BF3•OEt2

Chuan Zhu et al.

ORGANIC LETTERS (2012)

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Article Chemistry, Inorganic & Nuclear

Frustrated Lewis Pair Behavior of Intermolecular Annine/B(C6F5)3 Pairs

Tanja Voss et al.

ORGANOMETALLICS (2012)

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Article Chemistry, Inorganic & Nuclear

Reactivity of Lewis Acid Activated Diaza- and Dithiaboroles in Electrophilic Arene Borylation

S. A. Solomon et al.

ORGANOMETALLICS (2012)

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Article Chemistry, Organic

A Perspective on Direct Electrophilic Arene Borylation

Michael J. Ingleson

SYNLETT (2012)

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Article Chemistry, Multidisciplinary

A Boronium Ion with Exceptional Electrophilicity

Aleksandrs Prokofjevs et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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Article Chemistry, Multidisciplinary

Pinacol Boronates by Direct Arene Borylation with Borenium Cations

Alessandro Del Grosso et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

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Article Chemistry, Multidisciplinary

Simple inexpensive boron electrophiles for direct arene borylation

Alessandro Del Grosso et al.

CHEMICAL COMMUNICATIONS (2011)

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Article Chemistry, Multidisciplinary

Direct Conversion of Arylamines to Pinacol Boronates: A Metal-Free Borylation Process

Fanyang Mo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

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Review Chemistry, Multidisciplinary

C-H Activation for the Construction of C-B Bonds

Ibraheem A. I. Mkhalid et al.

CHEMICAL REVIEWS (2010)

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Article Chemistry, Organic

Synthesis of Pyridine-Borane Complexes via Electrophilic Aromatic Borylation

Naoki Ishida et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

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Article Chemistry, Inorganic & Nuclear

Activation of Terminal Alkynes by Frustrated Lewis Pairs

Chunfang Jiang et al.

ORGANOMETALLICS (2010)

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Article Chemistry, Inorganic & Nuclear

Chelate Restrained Boron Cations for Intermolecular Electrophilic Arene Borylation

Alessandro Del Grosso et al.

ORGANOMETALLICS (2010)

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Article Chemistry, Multidisciplinary

Terminal Alkyne Activation by Frustrated and Classical Lewis Acid/Phosphine Pairs

Meghan A. Dureen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

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