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Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C-N and C-O coupling reactions
Debashis Chakraborty
Published in Elsevier
2015
Volume: 781
   
Pages: 23 - 34
Abstract
This paper describes an efficient procedure for palladium(0)-catalyzed N-arylation and O-arylation of aryl halides by Ullmann-type cross coupling reaction under mild reaction conditions in a short reaction time. Two phosphine sulphide ligands and their corresponding Pd(0) complexes namely [Pd(p2S2)(dba)] and [Pd(pp3S4)(dba)], were synthesized, where p2S2 is 1,2-bis(diphenylphosphino)ethane disulfide, pp3S4 is tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide and dba is dibenzylideneacetone. Optimal reaction conditions were determined for the arylation reactions using iodobenzene and benzimidazole by varying temperature, solvent, base and catalyst loading. The cross coupling reactions were carried out taking iodobenzenes/bromobenzenes and a wide variety of substituted aryl amines/phenols/alcohols with different steric and electronic properties to afford the desired N-aryl amines/diaryl ethers/alkyl aryl ethers in good to excellent yield (70-94%). © 2015 Elsevier B.V. All rights reserved.
About the journal
JournalData powered by TypesetJournal of Organometallic Chemistry
PublisherData powered by TypesetElsevier
ISSN0022328X
Open AccessNo
Concepts (17)
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    Amines
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    Aromatic compounds
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    CATALYSTS
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    Electronic properties
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    Ethers
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    Loading
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    Palladium compounds
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    Phosphorus compounds
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    Reaction kinetics
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    SULFUR COMPOUNDS
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    Synthesis (chemical)
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    AIR STABLE
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    C-n bond formations
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    C-o bond formation
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    Cross-couplings
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    ULLMANN-TYPE REACTION
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    Chemical reactions