4-формилфенилборная кислота

Химические свойства

white to light yellow crystal powder

Использование

4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:

• Palladium-catalyzed Suzuki-Miyaura cross-coupling in water.
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides.
• Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.
• Triethylamine-catalyzed three-component Hantzsch condensations.
• Copper-catalyzed nitrations.
• Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta.
• Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides.
• Palladium-catalyzed aerobic oxidative cross-coupling reactions.
• The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.
• The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.
• The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.
• A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.

Синтез

Potassium phenyltrifluoroborate (184 mg, 1.00 mmol) was added to a solution of iron trichloride (185 mg, 1.10 mmol) in 3 mL of 1:1 THF/water. The mixture was stirred at room temperature for 30 min. The reaction mixture was then passed through a short column containing neutral absorption alumina. The alumina was then washed with a mixture of ethyl acetate/hexanes (2:1) to obtain 4-Formylphenylboronic acid (105 mg, 86%). [The boronic acid products can also be isolated by simple extraction techniques.]