24341-81-9Relevant academic research and scientific papers
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
Slabber, Cathryn A.,Grimmer, Craig D.,Robinson, Ross S.
, p. 122 - 128 (2013)
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
Diazaboryl-naphthyl-ketone: A New Scaffold with Bright Fluorescence, Aggregation-Induced Emission, and Application in the Quantitation of Trace Boronic Acids in Drug Intermediates
Hackney, Hannah E.,Paladino, Marco,Fu, Hao,Hall, Dennis G.
, p. 14324 - 14329 (2020)
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
Catalyst-free and eco-friendly synthesis of masked haloarylboronic acids R (alkyl or aryl)-B(dan) on water
Liao, Siwei,Hu, Xueyuan,Li, Yanwu,Wang, Xuetong,Li, Dan,Wang, Qiang,Wang, Yin,Huang, Xin,Xu, Ping,Wu, Huili,Li, Xianliang,Yuan, Jianyong
supporting information, (2021/05/31)
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.
Transition metal-free B(dan)-installing reaction (dan: naphthalene-1,8-diaminato): H-B(dan) as a B(dan) electrophile
Li, Jialun,Seki, Michinari,Kamio, Shintaro,Yoshida, Hiroto
supporting information, p. 6388 - 6391 (2020/06/21)
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.
Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids
Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu
, p. 164 - 171 (2018/12/05)
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.
Bench-Stable Sulfoxide-Based Boronates: Preparation and Application in a Tandem Suzuki Reaction
?ubiňák, Marek,Eigner, Václav,Tobrman, Tomá?
supporting information, p. 4604 - 4614 (2018/10/31)
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.).
NBN-Doped Conjugated Polycyclic Aromatic Hydrocarbons as an AIEgen Class for Extremely Sensitive Detection of Explosives
Wan, Wen-Ming,Tian, Di,Jing, Ya-Nan,Zhang, Xiao-Yun,Wu, Wei,Ren, Hao,Bao, Hong-Li
supporting information, p. 15510 - 15516 (2018/10/31)
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
A mild carbon-boron bond formation from diaryliodonium salts
Miralles,Romero,Fernández,Mu?iz
, p. 14068 - 14071 (2015/09/15)
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.
A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates
Churches, Quentin I.,Hooper, Joel F.,Hutton, Craig A.
, p. 5428 - 5435 (2015/06/16)
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.
Iron catalysis and water: A synergy for refunctionalization of boron
Wood, John L.,Marciasini, Ludovic D.,Vaultier, Michel,Pucheault, Mathieu
, p. 551 - 555 (2014/03/21)
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.
