Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 345, Issue 9-10, Pages 1146-1158Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200303067
Keywords
alkynes; aryl halides; C-C coupling; homogeneous catalysis; metallacycles; N ligands; palladium
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Oxime-derived chloro-bridged palladacycle 8a, derived from 4,4'-dichlorobenzophenone, is an efficient pre-catalyst for the copper- and amine-free Sonogashira coupling between terminal acetylenes and aryl iodides and aryl and vinyl bromides achieving turnover numbers (TON) of up to 72000. Catalyst 8a has also been shown as a effective promoter for the sila-Sonogashira coupling between 1-(trimethylsilyl)alkynes and aryl iodides and bromides in the presence of CuI or Bu4NBr as co-catalysts. This complex also catalyzes efficiently the homocoupling reaction (Glaser-type coupling) between 1-alkynes in NMP at room temperature with TONs of up to 1000. All the reactions can be performed under air and employing reagent-grade chemicals under very low loading conditions, which demonstrates the versatility and high activity of oxime-derived palladacycles.
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