- Solution-state 15N NMR and solid-state single-crystal XRD study of heterosubstituted diazaboroles and borinines prepared via an effective and simple microwave-assisted solvent-free synthesis
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A quick and simple, solvent-free synthesis of nitrogen-basedboroles and borinines derived from 1,2-diaminobenzene and 1,8-diaminonaphthalene is reported and compared with the traditional synthetic method. Characterization by 15N NMR spectroscop
- Slabber, Cathryn A.,Grimmer, Craig D.,Robinson, Ross S.
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- Diazaboryl-naphthyl-ketone: A New Scaffold with Bright Fluorescence, Aggregation-Induced Emission, and Application in the Quantitation of Trace Boronic Acids in Drug Intermediates
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This study describes the synthesis, structure, and photophysical properties of a new luminescent polyaromatic boronic acid scaffold, diazaboryl-naphthyl-ketones (DNKs). These stable compounds display extremely bright fluorescence, aggregation-induced emis
- Hackney, Hannah E.,Paladino, Marco,Fu, Hao,Hall, Dennis G.
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- Catalyst-free and eco-friendly synthesis of masked haloarylboronic acids R (alkyl or aryl)-B(dan) on water
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An environment-friendly methodology for the synthesis of R (alkyl or aryl)-B(dan) on water is described. 1,8-diamino naphthalene(danH2) was reacted with different types of organoboronic acids to furnish the products in moderate to excellent yields. A multi-gram scale reaction is also performed to ensure the scalability of the reaction.
- Liao, Siwei,Hu, Xueyuan,Li, Yanwu,Wang, Xuetong,Li, Dan,Wang, Qiang,Wang, Yin,Huang, Xin,Xu, Ping,Wu, Huili,Li, Xianliang,Yuan, Jianyong
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supporting information
(2021/05/31)
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- Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H-B(dan) as a B(dan) electrophile
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H-B(dan) was demonstrated to serve as a B(dan) electrophile, despite its highly diminished boron-Lewis acidity, leading to direct and transition metal-free approach to R-B(dan) of high synthetic utility upon treatment with Grignard reagents. Iterative cross-coupling of 5-bromo-2-pyridyl-B(dan), synthesized by the present method, was also achieved.
- Li, Jialun,Seki, Michinari,Kamio, Shintaro,Yoshida, Hiroto
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supporting information
p. 6388 - 6391
(2020/06/21)
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- Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids
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Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.
- Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu
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p. 164 - 171
(2018/12/05)
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- Bench-Stable Sulfoxide-Based Boronates: Preparation and Application in a Tandem Suzuki Reaction
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A set of novel aromatic and heteroaromatic bench-stable sulfoxide-based boronates was prepared. The structure of the boronates was established by means of X-ray crystallography, and the prepared boronates were successively used in Suzuki cross-coupling reactions under different conditions. We also developed a tandem Suzuki reaction so that a base is generated during the nucleophilic addition of Grignard reagents to 4-bromobenzaldehyde. The formed intermediates were smoothly coupled with the prepared boronates and the boronic acids under external base-free conditions. (Figure presented.).
- ?ubiňák, Marek,Eigner, Václav,Tobrman, Tomá?
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supporting information
p. 4604 - 4614
(2018/10/31)
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- NBN-Doped Conjugated Polycyclic Aromatic Hydrocarbons as an AIEgen Class for Extremely Sensitive Detection of Explosives
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A simple and efficient synthesis of NBN-doped conjugated polycyclic aromatic hydrocarbons (such as diazaborinines) has been accomplished by a catalyst-free intermolecular dehydration reaction at room temperature between boronic acid and diamine moieties w
- Wan, Wen-Ming,Tian, Di,Jing, Ya-Nan,Zhang, Xiao-Yun,Wu, Wei,Ren, Hao,Bao, Hong-Li
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supporting information
p. 15510 - 15516
(2018/10/31)
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- A mild carbon-boron bond formation from diaryliodonium salts
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The direct metal-free borylation of diaryliodonium salts with diboron reagents is now demonstrated to be a feasible process toward formation of aryl boronic esters without any additive or catalysts, and it can be extended to a two-step C-C coupling of both aryl groups of the initial diaryliodonium reagent.
- Miralles,Romero,Fernández,Mu?iz
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p. 14068 - 14071
(2015/09/15)
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- A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates
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We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.
- Churches, Quentin I.,Hooper, Joel F.,Hutton, Craig A.
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p. 5428 - 5435
(2015/06/16)
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- Iron catalysis and water: A synergy for refunctionalization of boron
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A new catalytic system has been optimized to promote the conversion of boron species into others. FeCl3 associated with imidazole and water favors boron refunctionalization under mild conditions. Georg Thieme Verlag Stuttgart New York.
- Wood, John L.,Marciasini, Ludovic D.,Vaultier, Michel,Pucheault, Mathieu
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p. 551 - 555
(2014/03/21)
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- Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid
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Phenylboronic acid (2) reacts quantitatively by ball-milling in the solid state with o-phenylendiamine, 1,8-diaminonaphthalene, anthranilic acid, pyrocatechol, pyrogallol, pinacol, bicyclic cis-diols, mannitol, and inositol to form the five- or six-membered cyclic phenyl-boronic amides or esters. Catalysts or other auxiliaries are strictly excluded as they are not required and would have to be removed after the reactions. These varied model reactions provide pure protected products without the necessity of further purifying workup and the potential for protection chemistry is demonstrated. Some of the reactions can also be quantitatively performed if stoichiometric mixtures of the reactants are co-ground or co-milled and heated to appropriate temperatures either below the eutectics or above the melting points. The temperatures are much higher in the latter case. Similar reactions in solution suffer from less than 100% yield of the mostly sensitive compounds that are difficult to purify and thus create much waste. The hydrolysis (de-protection) conditions of the products are rather mild in most cases. Therefore, this particularly easy access to heteroboroles, heteroborolanes, heteroborinones, heteroborines, and heteroborinines is highly valuable for their more frequent use in protective syntheses.
- Kaupp, Gerd,Naimi-Jamal, M. Reza,Stepanenko, Vladimir
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p. 4156 - 4160
(2007/10/03)
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