Synthesis of large ring macrocycles (12-18) by recyclable palladium-complexed dendrimers on silica gel catalyzed intramolecular cyclocarbonylation reactions.
Intramolecular cyclocarbonylation reactions with palladium-complexed dendrimers on silica gel as catalysts are very effective for the synthesis of twelve- to eighteen-membered ring macrocycles. This process can tolerate a wide variety of functional groups, including halide, ether, ketone, and ester. The heterogeneous dendritic catalysts facilitate excellent substrate reactivity, affording oxygen-, nitrogen-, or sulfur-containing tricyclic heterocycles in 70-92 % yields. Importantly, these systems are easily recovered by simple filtration and reused several times with only a slight loss of activity.
Lu
Shui-Ming
SM
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, Ottawa, Ontario, K1N 6N5, Canada.
Alper
Howard
H
D002384:Catalysis; D003500:Cyclization; D050091:Dendrimers / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry*
D050091:Dendrimers; D047028:Macrocyclic Compounds; D009942:Organometallic Compounds; D010165:Palladium; D058428:Silica Gel; D012822:Silicon Dioxide