(2-METHOXY-1-NAPHTHYL)BORONIC ACID

• Design of phosphorus C,P-ligands for environmentally benign cross-coupling reactions
• Sterically hindered Suzuki-Miyaura coupling
• Palladium-catalyzed cross-coupling reactions
• Deboronation homocoupling reactions
• Copper-catalyzed N-arylation of imidazoles
• Stereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling

121-43-7

3401-47-6

104116-17-8

A tetrahydrofuran (THF, 50 mL) solution of 1-bromo-2-methoxynaphthalene (7.67 g, 32.36 mmol) was slowly added dropwise to a THF solution (15 mL) of magnesium shavings (0.905 g, 37.2 mmol) in a flame-dried reaction vessel protected by argon. The reaction mixture was stirred at room temperature for 2 hours, followed by warming to 50 °C and continued stirring for 1 hour. Upon completion of the reaction, the mixture was cooled to -78 °C and trimethyl borate (11.4 mL, 101.7 mmol) was slowly added. After remaining at -78 °C for 2 h, the reaction mixture was gradually warmed to room temperature and stirred overnight. After addition of water (40 mL), THF was removed by distillation under reduced pressure. the aqueous phase was extracted with dichloromethane, the organic phases were combined and dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated. The target product 2-methoxy-1-naphthylboronic acid was obtained by recrystallization from dichloromethane as a white powder in 80% yield. The structure of the product was confirmed by 1H NMR (400.14 MHz, CDCl3) and 13C{1H} NMR (75.47 MHz, [D6]DMSO).