42409-65-4Relevant academic research and scientific papers
Synthesis and structural analysis of conjugated benzoxazaborine derivatives
Ohishi, Tomoyuki,Igarashi, Kaori,Kadosono, Hiroki,Kikkawa, Shoko,Azumaya, Isao,Yokoyama, Akihiro
supporting information, p. 4153 - 4157 (2018/10/24)
Benzoxazaborine derivatives were synthesized by the dehydration condensation reaction of 2-aminobenzyl alcohols with arylboronic acids. The insensitivity of the benzoxazaborines to hydrolysis allowed these compounds to be isolated by silica gel column chr
Azaborininones: Synthesis and Structural Analysis of a Carbonyl-Containing Class of Azaborines
Davies, Geraint H. M.,Mukhtar, Asma,Saeednia, Borna,Sherafat, Fatemeh,Kelly, Christopher B.,Molander, Gary A.
, p. 5380 - 5390 (2017/05/24)
An approach to access azaborininones (carbonyl-containing, boron-based heterocyclic scaffolds) using simple reagents and conditions from both organotrifluoroborates and boronic acids is described. An inexpensive, common reagent, SiO2, was found to serve as both a fluorophile and desiccant to facilitate the annulation process across three different azaborininone platforms. Computational analysis of some of the cores synthesized in this study was undertaken to compare the azaborininones with the analogous carbon-based heterocyclic systems. Computationally derived pKa values, NICS aromaticity calculations, and electrostatic potential surfaces revealed a unique isoelectronic/isostructural relationship between these azaborines and their carbon isosteres that changed based on boron connectivity. Correlation to experimentally derived data supports the computational findings.
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.
