Synthesis of 9‐O‐Arylated Berberine with a Polystyrene Resin Supported Copper(II) Catalyst

Abstract

A series of polyfluorobenzene, pyridine and aniline substituted berberine derivatives (3 b–3 h) were prepared via resin‐supported Cu(II) catalyzed cross‐coupling reactions of tetrahydroberberrubine with iodoarenes and subsequent I2 oxidation. The best catalyst, a polyethyleneimine functionalized polystyrene supported Cu2+ (PSAPA⋅Cu(II)), could be reused for at least 5 runs without significant loss of catalytic activity. Comparative studies on the morphology and porous structures of the materials suggested a catalyst with a moderate specific surface area and larger pore diameters was more active in catalyzing the cross‐coupling reactions.

C9-Aryl-substituted berberine derivatives with tunable AIE properties for cell imaging application

“…[10][11][12][13][14] However, modifications at the C9 position of berberine mainly concentrate on the etherification or esterification of berberrubine, leading to C9-O-substituted berberine derivatives. [15][16][17] There are few reports on the direct C9-substitution of berberine, 18 which is a significant research gap for the derivation of berberine.…”