Pd-catalyzed C-C cross-coupling reactions within a thermoresponsive and pH-responsive and chelating polymeric hydrogel.
A porous, thermoresponsive and pH-responsive, and chelating hydrogel of poly(N-isopropylacrylamide)-co-poly[2-methacrylic acid 3-(bis-carboxymethylamino)-2-hydroxypropyl ester] (PNIPAM-co-PMACHE) is proposed as both a reaction medium and the Pd catalyst support for organic synthesis. Organic synthesis within the PNIPAM-co-PMACHE hydrogel has three merits. First, organic reactions such as Suzuki and Heck reactions within the hydrogel can be accelerated due to the enriched Pd catalyst and reactants within the hydrogel by the reversible deswelling/swelling. Second, organic synthesis within the PNIPAM-co-PMACHE hydrogel, which holds about approximately 300 times of water and is similar to the environmentally benign reaction medium of water, can be performed efficiently without surfactant or cosolvent being added. Third, the PNIPAM-co-PMACHE hydrogel itself and the therein-immobilized Pd catalyst can be easily recycled since the hydrogel/Pd composite can reversibly swell/deswell.
Wang
Yao
Y
Key Laboratory of Functional Polymer Materials of Ministry of Education, Institute of Polymer Chemistry, Nankai University, Tianjin 300071, China.
Zhang
Jianzheng
J
Zhang
Wangqing
W
Zhang
Minchao
M
D000180:Acrylic Resins / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002614:Chelating Agents / Q000138:chemical synthesis* / Q000737:chemistry; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D010165:Palladium / Q000737:chemistry*; D010316:Particle Size; D016062:Porosity; D013499:Surface Properties; D013696:Temperature
D000180:Acrylic Resins; D002614:Chelating Agents; C551676:poly(N-isopropylacrylamide)-co-poly(2-methacrylic acid 3-(bis-carboxymethylamino)-2-hydroxypropyl ester); C052970:poly-N-isopropylacrylamide; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate; D010165:Palladium