2479-64-3Relevant articles and documents
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
Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components
Davies, Geraint H. M.,Molander, Gary A.
, p. 3771 - 3779 (2016/05/24)
The azaborine motif provides a unique opportunity to develop core isosteres by inserting B-N units in place of C-C bonds within aromatic scaffolds, creating new pseudoaromatic building blocks that retain comparable structural features. Previous synthetic routes to the 1,3,2-benzodiazaborole core have used organoboron dichlorides and boronic acids as the boron precursors. The transformation developed herein utilizes entirely bench stable starting materials, including organotrifluoroborates, enabling a wider array of substrate analogues under facile reaction conditions. Furthermore, physical, structural, and electronic properties of these compounds were explored computationally to understand the influence of the B-N replacement on the structure, aromaticity, and isosteric viability of these analogues.
Palladium-catalysed cross-coupling reaction of ultra-stabilised 2-aryl-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole compounds with aryl bromides: A direct protocol for the preparation of unsymmetrical biaryls
Sithebe, Siphamandla,Robinson, Ross S.
supporting information, p. 1107 - 1113 (2014/06/09)
There has been a significant interest in organoboron compounds such as arylboronic acids, arylboronate esters and potassium aryltrifluoroborate salts because they are versatile coupling partners in metal-catalysed cross-coupling reactions. On the other hand, their nitrogen analogues, namely, 1,3,2-benzodiazaborole-type compounds have been studied extensively for their intriguing absorption and fluorescence characteristics. Here we describe the first palladium-catalysed Suzuki-Miyaura cross-coupling reaction of easily accessible and ultra-stabilised 2-aryl-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole derivatives with various aryl bromides. Aryl bromides bearing electron-withdrawing, electron-neutral and electron-donating substituents are reacted under the catalytic system furnishing unsymmetrical biaryl products in isolated yields of up to 96% in only 10 minutes.
Boric acid-catalyzed direct condensation of carboxylic acids with benzene-1,2-diamine into benzimidazoles
Maras, Nenad,Kocevar, Marijan
experimental part, p. 1860 - 1874 (2011/12/02)
The applicability of boric acid catalysis for the direct condensation of carboxylic acids with benzene-1,2-diamine to give 2-substituted benzimidazoles was investigated. It was found that catalytic amounts (5-10 mol-%) of boric acid efficiently promote the cyclocondensation of aliphatic carboxylic acids in refluxing toluene. In addition, the relatively neutral conditions allow the use of acid-sensitive substrates and give rise to specific transformations and selectivities that are not observed with some classical methods. Benzoic acids were found to be less reactive than aliphatic acids and thus require refluxing xylene for better efficiency. Phenylboronic acid was found to be inactive as a catalyst due to its rapid consumption by condensation with benzene-1,2-diamine to give a 2-phenylbenzodiazaborole. Copyright
Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid
Kaupp, Gerd,Naimi-Jamal, M. Reza,Stepanenko, Vladimir
, p. 4156 - 4160 (2007/10/03)
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.
