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.

doi:10.1016/j.jorganchem.2012.09.018

Cited by 14 publications

(3 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Following the general procedure B, 2g was obtained from p-anisidine (151.9 mg, 1.0 mmol) and 1,8diaminonaphtalene (158.2 mg, 1.0 mmol) as a brown solid (113.9 mg, 41.5%) after preparative TLC on silica, eluting with pentane/ (85:15). The 1 H and 13 C data were consistent with those reported in the literature: 34 General Procedure C for Biaryl Compounds Synthesis. To a solution of aniline (93.1 mg, 1.0 mmol, 1.0 equiv) in HCl (2.1 M in water, 1.2 mL, 2.5 mmol, 2.5 equiv) at 0 °C was added a solution of NaNO 2 (2.4 M in water, 0.5 mL, 1.2 mmol, 1.2 equiv) dropwise, and the reaction mixture was stirred for 15 min at 0 °C.…”

Section: ■ Experimental Sectionsupporting

confidence: 88%

“…Following the general procedure B, 2g was obtained from p -anisidine (151.9 mg, 1.0 mmol) and 1,8-diaminonaphtalene (158.2 mg, 1.0 mmol) as a brown solid (113.9 mg, 41.5%) after preparative TLC on silica, eluting with pentane/EtOAc (85:15). The 1 H and 13 C data were consistent with those reported in the literature: mp 128–131 °C; ν max (film)/cm –1 3408, 1723, 1595, 1492, 1406, 1224, 1179, 1085, 1028, 818, 760; 1 H NMR (400.0 MHz; CDCl 3 ) δ H = 7.57 (d, J = 8.1 Hz, 2H, ArH), 7.15 (t, J = 7.4 Hz, 2H, ArH), 7.06 (d, J = 8.1 Hz, 2H, ArH), 6.97 (d, J = 7.4 Hz, 2H, ArH), 6.40 (d, J = 7.4 Hz, 2H, ArH), 5.98 (br s, 2H, 2 × NH), 3.84 (s, 3H, CH 3 ); 13 C NMR (100.6 MHz; CDCl 3 ) δ C = 161.5 (ArC), 141.4 (ArC), 136.5 (ArC), 133.2 (2 × ArCH), 127.8 (2 × ArCH), 119.8 (2 × ArC), 117.8 (2 × ArCH), 114.0 (2 × ArCH), 106.1 (2 × ArCH), 55.3 (CH 3 ); 11 B NMR (128.4 MHz; CDCl 3 ) δ B = 29.3 (br).…”

Section: Experimental Sectionsupporting

confidence: 87%

See 1 more Smart Citation

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

et al. 2014

View full text Add to dashboard Cite

show abstract

Section: ■ Experimental Sectionsupporting

confidence: 88%

Section: Experimental Sectionsupporting

confidence: 87%

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

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Alternatively, three-coordinate boron compounds functionalized with 1,3,2-benzodiazaborole units are greatly stabilised by electron back-donation from the two nitrogen atoms to the empty boron p z -orbital (Fig. 2, compound 6 ) [13–14]. …”

Section: Introductionmentioning

confidence: 99%

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

Sithebe¹,

Robinson²

2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThere 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.

show abstract

NBN‐Doped Conjugated Polycyclic Aromatic Hydrocarbons as an AIEgen Class for Extremely Sensitive Detection of Explosives

et al. 2018

View full text Add to dashboard Cite

As imple and efficient synthesis of NBN-doped conjugated polycyclic aromatic hydrocarbons (sucha sd iazaborinines) has been accomplished by ac atalyst-free intermolecular dehydration reaction at room temperature between boronic acid and diamine moieties with yields up to 99 %. Polycyclic aromatic hydrocarbons with as ix-membered NBN ring are an ew class of aggregation-induced emissive luminogens.E xtremely sensitive detection of ppb levels of TNT by phenyl naphthodiazaborinine is straightforward. Visual detection of TNT is illustrated by fabrication of TNT test strips, which can detect as little as 100 ng of TNT powder.This simple and sensitive detection of TNT has potential applications in the area of public safety and security against terrorist activities.Doping of polycyclica romatic hydrocarbons (PAHs) with boron-nitrogen units,t hat is,i soelectronic and isosteric replacement of aC =Cb ond with aB ÀNb ond (Scheme 1), has emerged as av ersatile strategy for the preparation of novel hybrid PA Hs with unusual and attractive optical, electronic,a nd chemical properties that are absent from their C=Cc ongeners. [1] Them olecular design of boronnitrogen-doped PA Hs therefore expands the structure and functionality library of p-systems,and such chemistry is highly desirable in the development of useful materials. [2] For example,since the pioneering work on BN doped p-systems, namely azaborinines,b yD ewar and White in the 1960s, considerable research effort has been devoted by,for example Ashe,L iu, Braunschweig,S chäfer,a nd Jäkle [3] to the synthesis,p roperties,a nd reactivity of azaborinines.S ince Weberspioneering work on NBN-doped compounds,specifically diazaborinines,t here have been numerous investigations of their synthesis,o na ccount of their potential applications as drugs and as reagents that can be used in the Suzuki-Mayaura reaction. [4] Although considerable progress has been made in boron-nitrogen doped p-systems,t he currently available preparative methods suffer from the need for rigorous reaction conditions including the requirement for conditions which are air-and/or moisture-free,multiple steps and unsatisfactory total yield. Finding as imple and mild strategy with which to synthesize boron-nitrogen-doped PA Hs is therefore significant and highly desirable.Boron-containing p-systems have attracted considerable research attention since the 1960s due to their desirable optical, electronic, and sensory properties. [5] With the presence of an empty porbital of the boron center in p-systems, such compounds are luminogens and are widely utilized as such. [6] Tr aditional luminogens fluoresce strongly in dilute solution but are subject to aggregation-caused quenching (ACQ) [7] and the luminogens are quenched at higher concentrations or in aggregation states.I n2 001, Tang described the aggregation-induced emission (AIE) of luminogens (AIEgens), [8] which fluoresce weakly when dissolved, but emit strongly when aggregated. As an important class of luminogens,b oron containing p-systems featuring AIE,...

show abstract

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

Cited by 14 publications

References 24 publications

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

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

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

NBN‐Doped Conjugated Polycyclic Aromatic Hydrocarbons as an AIEgen Class for Extremely Sensitive Detection of Explosives

Contact Info

Product

Resources

About