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RESEARCH PRODUCT
Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling
Konstantin V. LuzyaninMikhail A. KinzhalovVadim Yu. KukushkinM. Fátima C. Guedes Da SilvaM. Fátima C. Guedes Da SilvaMatti HaukkaSvetlana A. TimofeevaTatyana M. BuslaevaElena A. ValishinaElena A. ValishinaVadim P. BoyarskiyArmando J. L. Pombeirosubject
Process Chemistry and TechnologyArylchemistry.chemical_elementSonogashira couplingDecompositionCopperMedicinal chemistryCatalysisCatalysischemistry.chemical_compoundAcetylenechemistryOrganic chemistryPhysical and Theoretical ChemistryCarbeneta116Palladiumdescription
Abstract The metal-mediated coupling between cis-[PdCl2(CNR1)2] [R1 = cyclohexyl (Cy) 1, t-Bu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3 4] and hydrazones H2NN CR2R3 [R2, R3 = Ph 5; R2, R3 = C6H4(OMe-4) 6; R2/R3 = 9-fluorenyl 7; R2 = H, R3 = C6H4(OH-2) 8] provided carbene complexes cis-[PdCl2{C(N(H)N CR2R3) N(H)R1}(CNR1)] (9–24) in good (80–85%) yields. Complexes 9–24 showed high activity [yields up to 99%, and turnover numbers (TONs) up to 3.7 × 104] in the Sonogashira coupling of various aryl iodides with a range of substituted aromatic alkynes without the need of copper co-catalyst. The catalytic procedure runs at 80 °C for 1 h in EtOH using K2CO3 as a base. No formation of homocoupling or acetylene decomposition products was observed. Designed copper-free Sonogashira system can also run at room temperature giving target products with yields up to 87% and TONs up to 87.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-12-01 | Journal of Molecular Catalysis A: Chemical |