Synthesis of 9‐O‐Arylated Berberine with a Polystyrene Resin Supported Copper(II) Catalyst. Issue 16 (27th April 2021)

• Record Type: Journal Article
• Authors: Meng, Qi; Zhang, Lian; Zhu, Xinhui; Teng, Qiaoqiao
• Is Part Of: ChemistrySelect. Volume 6:Issue 16(2021)
• Page Start: 4011
• Page End: 4014
• Publication Date: 2021-04-27
• Subjects: Berberine -- Cross-coupling -- Heterogeneous catalysis -- Recycling -- Resins; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202100525
• Languages: English
• ISSNs: 2365-6549

Abstract

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 Cu 2+ (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. Abstract : A series of 9‐O‐arylated berberine derivatives were prepared via Ullmann type cross‐coupling reactions catalyzed by a polyethyleneimine‐polystyrene supported Cu(II) followed by oxidation reactions. In comparison with molecular catalysts, the immobilized catalyst is not only more reactive, but could be reused for at least 5 runs without significant loss of catalytic activity.