Publication:
Unveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the alpha-alkylation of ketones with primary alcohols

dc.contributor.coauthorOvezova, Mamajan
dc.contributor.coauthorÇetinkaya, Bekir
dc.contributor.coauthorGülcemal, Süleyman
dc.contributor.departmentDepartment of Chemistry
dc.contributor.kuauthorEroğlu, Zafer
dc.contributor.kuauthorMetin, Önder
dc.contributor.schoolcollegeinstituteCollege of Sciences
dc.date.accessioned2024-11-09T13:09:11Z
dc.date.issued2021
dc.description.abstractWe report herein the synthesis of four new Pd-PEPPSI complexes with backbone-modified N-heterocyclic carbene (NHC) ligands and their application as catalysts in the alpha-alkylation of ketones with primary alcohols using a borrowing hydrogen process and tandem Suzuki-Miyaura coupling/alpha-alkylation reactions. Among the synthesized Pd-PEPPSI complexes, complex 2c having 4-methoxyphenyl groups at the 4,5-positions and 4-methoxybenzyl substituents on the N-atoms of imidazole exhibited the highest catalytic activity in the alpha-alkylation of ketones with primary alcohols (18 examples) with yields reaching up to 95%. Additionally, complex 2c was demonstrated to be an effective catalyst for the tandem Suzuki-Miyaura-coupling/alpha-alkylation of ketones to give biaryl ketones with high yields. The heterogeneous nature of the present catalytic system was verified by mercury poisoning and hot filtration experiments. Moreover, the formation of NHC-stabilized Pd(0) nanoparticles during the alpha-alkylation reactions was identified by advanced analytical techniques.
dc.description.fulltextYES
dc.description.indexedbyWOS
dc.description.indexedbyScopus
dc.description.indexedbyPubMed
dc.description.issue31
dc.description.openaccessYES
dc.description.publisherscopeInternational
dc.description.sponsoredbyTubitakEuTÜBİTAK
dc.description.sponsorshipEge University Scientific Research Projects Coordination
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TÜBİTAK)
dc.description.sponsorship2211/C National Ph.D. Scholarship Program in the Priority Fields in Science and Technology
dc.description.sponsorshipCouncil of Higher Education of Turkey 100/2000 CoHE Doctoral Scholarship
dc.description.sponsorshipTurkish Academy of Science (TUBA)
dc.description.sponsorshipTurkiye Scholarships Fellowship
dc.description.versionAuthor's final manuscript
dc.description.volume50
dc.identifier.doi10.1039/d1dt01704g
dc.identifier.eissn1477-9234
dc.identifier.embargoNO
dc.identifier.filenameinventorynoIR03362
dc.identifier.issn1477-9226
dc.identifier.quartileQ1
dc.identifier.scopus2-s2.0-85112441725
dc.identifier.urihttps://doi.org/10.1039/d1dt01704g
dc.identifier.wos678767400001
dc.keywordsAlkylation reactions
dc.keywordsBorrowing hydrogens
dc.keywordsCatalytic system
dc.keywordsFiltration experiments
dc.keywordsN-heterocyclic carbene ligands
dc.keywordsN-heterocyclic carbenes
dc.keywordsPrimary alcohols
dc.keywordsSuzuki-Miyaura coupling
dc.language.isoeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.grantnoFYL-2019-21171
dc.relation.ispartofDalton Transactions
dc.relation.urihttp://cdm21054.contentdm.oclc.org/cdm/ref/collection/IR/id/10139
dc.subjectInorganic chemistry
dc.subjectNuclear chemistry
dc.titleUnveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the alpha-alkylation of ketones with primary alcohols
dc.typeJournal Article
dspace.entity.typePublication
local.contributor.kuauthorMetin, Önder
local.contributor.kuauthorEroğlu, Zafer
local.publication.orgunit1College of Sciences
local.publication.orgunit2Department of Chemistry
relation.isOrgUnitOfPublication035d8150-86c9-4107-af16-a6f0a4d538eb
relation.isOrgUnitOfPublication.latestForDiscovery035d8150-86c9-4107-af16-a6f0a4d538eb
relation.isParentOrgUnitOfPublicationaf0395b0-7219-4165-a909-7016fa30932d
relation.isParentOrgUnitOfPublication.latestForDiscoveryaf0395b0-7219-4165-a909-7016fa30932d

Files

Original bundle

Now showing 1 - 1 of 1
Thumbnail Image
Name:
10139.pdf
Size:
1.15 MB
Format:
Adobe Portable Document Format