Practical Reactions / Bond Formation

Suzuki-Miyaura Cross Coupling

A screw-top test tube equipped with a magnetic stir bar was charged with 6a or 7a (0.02 mmol, 2 mol %), arylboronic acid (1.50 mmol, 1.50 equiv), and aryl halide (if solid, 1.00 mmol, 1.00 equiv), and the tube was sealed with a Teflon screw-cap septum. The vessel was evacuated and back filled with argon (this process was repeated a total of three times), and the aryl halide, if liquid (1.00 mmol, 1.00 equiv) was added at this time. Anhydrous THF (2 mL) and 0.5 M aq. K3PO4 solution (4 mL) were then added via syringe, and the reaction mixture was stirred for 30 min at room temperature. The reaction mixture was diluted with EtOAc (10 mL) and H2O (10 mL), and the layers were separated. The aqueous layer was extracted with additional EtOAc (3 × 5 mL). The combined organic layers were dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated, and the resulting residue was purified by flash chromatography using a Biotage Isolera Four system with a SNAP 25 g cartridge to afford the desired product. 5-(2,6-Difluorophenyl)-2-methylbenzo[d]thiazole. White solid.
Yield from 6a: 248 mg, 95%. Yield from 7a: 255 mg, 98%.

※6a: XPhos Pd G4

2014/4/11
10.1021/jo500355k

XPhos Pd G4 / 1599466-81-5

鈴木・宮浦クロスカップリング Suzuki-Miyaura Cross Coupling
Suzuki Coupling

G3 and G4 Buchwald Precatalysts