4-Cyanophenylboronic acid

4-Cyanophenylboronic acid Structure
4-Cyanophenylboronic acid structure
Common Name 4-Cyanophenylboronic acid
CAS Number 126747-14-6 Molecular Weight 146.94
Density 1.3±0.1 g/cm3 Boiling Point 355.9±44.0 °C at 760 mmHg
Molecular Formula C7H6BNO2 Melting Point >350 °C(lit.)
MSDS Chinese USA Flash Point 169.0±28.4 °C

Use of dimethyl carbonate as a solvent greatly enhances the biaryl coupling of aryl iodides and organoboron reagents without adding any transition metal catalysts.

Chem. Commun. (Camb.) 23th ed., 48 , 2912-2914, (2012)

The coupling reaction of aryl iodides with arylboronic acids to give biaryl compounds can be efficiently performed without adding a transition metal catalyst. The key to success is the use of dimethyl carbonate as a solvent. This finding provides a new strate...

Ruthenium(0)-catalyzed sp3 C-H bond arylation of benzylic amines using arylboronates.

Org. Lett. 7th ed., 14 , 1930-1933, (2012)

A Ru-catalyzed direct arylation of benzylic sp(3) carbons of acyclic amines with arylboronates is reported. This highly regioselective and efficient transformation can be performed with various combinations of N-(2-pyridyl) substituted benzylamines and arylbo...

3,5-Diaryl-2-aminopyridines as a novel class of orally active antimalarials demonstrating single dose cure in mice and clinical candidate potential.

J. Med. Chem. 7th ed., 55 , 3479-3487, (2012)

A novel class of orally active antimalarial 3,5-diaryl-2-aminopyridines has been identified from phenotypic whole cell high-throughput screening of a commercially available SoftFocus kinase library. The compounds were evaluated in vitro for their antiplasmodi...

Fullerenyl boronic esters: ferric perchlorate-mediated synthesis and functionalization.

Org. Lett. 7th ed., 14 , 1800-1803, (2012)

Fullerenyl boronic esters have been prepared by a ferric perchlorate-promoted reaction of [60]fullerene with various arylboronic acids. The obtained fullerenyl boronic esters could undergo further functionalization with diols to afford C(60)-fused dioxane/dio...

Phosphine-free Suzuki-Miyaura cross-coupling in aqueous media enables access to 2-C-aryl-glycosides.

Org. Lett. 7th ed., 14 , 1728-1731, (2012)

A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aque...

Synthesis of new trisulfonated calix[4]arenes functionalized at the upper rim, and their complexation with the trimethyllysine epigenetic mark.

Org. Lett. 6th ed., 14 , 1512-1515, (2012)

A synthetic route to produce a new family of trisulfonated calix[4]arenes bearing a single group, selectively introduced, that lines the binding pocket is reported. Ten examples, including new sulfonamide and biphenyl-substituted hosts, each with additional b...

Ligand-free copper-catalyzed coupling of nitroarenes with arylboronic acids Zhang, J.; et al.

Green Chem. 4th ed., 14 , 912-916, (2012)

Highly effective synthesis of C-5-substituted 2'-deoxyuridine using Suzuki-Miyaura cross-coupling in water Sartori, G.; et al.

Synthesis 5th ed., 44 , 767-772, (2012)

Chan-Lam-type S-arylation of thiols with boronic acids at room temperature.

J. Org. Chem. 6th ed., 77 , 2878-2884, (2012)

In this work, an efficient CuSO(4)-catalyzed S-arylation of thiols with aryl and heteroaryl boronic acids at room temperature is established. This catalytic system can tolerate a wide variety of thiols and arylboronic acids in the presence of only 5 mol % of ...

Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents.

J. Med. Chem. 47 , 3658-3664, (2004)

2-[5-(4-Amidinophenyl)-furan-2-yl]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-6-carboxamidine acetate salt (7) was synthesized from 2-[5-(4-cyanophenyl)-furan-2-yl]-imidazo[1,2-a]pyridine-6-carbonitrile (4a), through the bis-O-acetoxyamidoxime followed by hydr...