95752-86-6

Usage

Uses

2-Formylphenylboronic Acid Neopentyl Glycol Ester

InChI:InChI=1/C12H15BO3/c1-12(2)8-15-13(16-9-12)11-6-4-3-5-10(11)7-14/h3-7H,8-9H2,1-2H3

Upstream product

• 40138-16-7 2-formylbenzene boronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 6852-58-0 N-benzylidene tert-butylamine 
• 100-52-7 benzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 

Downstream Products

• 1400888-17-6 2-(2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-1H-anthra[1,2-d]imidazole-6,11-dione 
• 1253976-99-6 C₂₀H₂₁BO₃ 

Relevant academic research and scientific papers

Transient imine as a directing group for the metal-free o-C-H borylation of benzaldehydes

Organoboron reagents are important synthetic intermediates and have wide applications in synthetic organic chemistry. The selective borylation strategies that are currently in use largely rely on the use of transition-metal catalysts. Hence, identifying much milder conditions for transition-metal-free borylation would be highly desirable. We herein present a unified strategy for the selective C-H borylation of electron-deficient benzaldehyde derivatives using a simple metal-free approach, utilizing an imine transient directing group. The strategy covers a wide spectrum of reactions and (i) even highly sterically hindered C-H bonds can be borylated smoothly, (ii) despite the presence of other potential directing groups, the reaction selectively occurs at the o-C-H bond of the benzaldehyde moiety, and (iii) natural products appended to benzaldehyde derivatives can also give the appropriate borylated products. Moreover, the efficacy of the protocol was confirmed by the fact that the reaction proceeds even in the presence of a series of external impurities.

Rhodium-catalyzed addition-spirocyclization of arylboronic esters containing β-aryl α,β-unsaturated ester Moiety

Abstract In this study, we developed a rhodium(I)-catalyzed spiro-cyclization. The reaction includes 1,4-rhodium migration and provides a route for forming spirocyclic 1-indanones.

A-D-A sensors based on naphthoimidazoledione and boronic acid as turn-on cyanide probes in water

(Chemical Equation Presented) Three fluorescence sensors based on naphthoquinoneimidazole and boronic acid (A-D-A system) have been developed with high selectivity for cyanide in water. The fluorescence band at 460 nm was switched on upon substitution of

An efficient synthesis of sterically hindered arylboronic acids

Boronic acids are important intermediates and molecular recognition moieties in a wide variety of applications. In our research, we have found that the synthesis of ortho-substituted arylboronic acids is problematic with the commonly used bis(pinacolato)diboron in palladium-mediated borylation reactions. As a substitute, we have found that bis(neopentyl glycolato)diboron is a much more efficient borylation agent for the synthesis of sterically hindered ortho-substituted arylboronic acids.

Suzuki cross-coupling reaction of sterically hindered aryl boronates with 3-iodo-4-methoxybenzoic acid methylester

The cross-coupling reaction of 3-iodo-4-methoxybenzoic acid methylester with sterically hindered arylboronic esters and especially 5,5-dimethyl-2-mesityl-1,3,2-dioxaborinane, is reported. The optimisation of the process in order to obtain biaryls in good yield by using anhydrous benzene at reflux and sodium phenoxide in the presence of 0.06 equiv. of Pd(PPh3)4 is described. (C) 2000 Elsevier Science Ltd.

On the Chemistry of Binding Sites, IV: On an Unusual Increase in Reactivity of Arylboronic Acids by Neighbouring Groups

ortho-Substituted arylboronic acids were investigated for subsequent use as binding sites.The introduction of different aminomethyl groupings resulted in a strong acceleration of the adjustment of the equilibrium of the esterification with diols as well as the transesterification of such esters.The rate of the transesterification was investigated with suitable systems by dynamic NMR spectroscopy.According to an estimation the enhancement compared with the unsubstituted compound amounted to 8 orders of magnitude.Most of the compounds showed a strong B-N-coordination as was shown by 11B NMR.There proved, however, to be no simple relation between B-N-coordination and the catalytic activity of the neighbouring groups.Neighbouring groups containing oxygen, sulfur, and fluorine showed no enhancement of esterification or transesterification and no coordination with the boron.