Show simple item record

dc.creatorBecica, Joseph
dc.creatorHruszkewycz, Damian
dc.creatorSteves, Janelle
dc.creatorElward, Jennifer
dc.creatorLeitch, David
dc.creatorDobereiner, Graham
dc.date.accessioned2020-04-22T14:17:23Z
dc.date.available2020-04-22T14:17:23Z
dc.date.issued2019-06-09
dc.identifier.citationBecica, Joseph; Hruszkewycz, Damian; Steves, Janelle; Elward, Jennifer; Leitch, David; Dobereiner, Graham (2019): High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides. ChemRxiv. Preprint. https://doi.org/10.26434/chemrxiv.9108461.v2
dc.identifier.doihttp://dx.doi.org/10.34944/dspace/50
dc.identifier.urihttp://hdl.handle.net/20.500.12613/63
dc.description.abstractSulfonamides are poor nucleophiles in Pd C-N coupling catalysis, hindering synthesis of densely-functionalized N,N-diaryl sulfonamide motifs relevant to medicinal chemistry. Through targeted high-throughput experimentation (HTE), we have identified the Pd/AdBippyPhos catalyst system as an effective and general method to construct this difficult to access moiety. In particular, AdBippyPhos is critical for the installation of heteroaromatic groups. Computational steric parameterization of the investigated ligands reveals the potential importance of remote steric demand, where a large cone angle combined with an accessible Pd center is correlated to successful catalysts for C-N coupling reactions.
dc.format.extent6 pages
dc.languageEnglish
dc.language.isoeng
dc.relation.ispartofFaculty/ Researcher Works
dc.relation.isreferencedbyChemRxiv
dc.rightsAttribution-NonCommercial-NoDerivs CC BY-NC-ND
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectSulfonamides
dc.subjectHeterocycles
dc.subjectPalladium
dc.subjectPhosphine parameterization
dc.subjectHigh throughput experimentation
dc.titleHigh-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides
dc.typeText
dc.type.genrePre-print
dc.description.departmentChemistry
dc.relation.doihttps://doi.org/10.26434/chemrxiv.9108461.v2
dc.ada.noteFor Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
dc.description.schoolcollegeTemple University. College of Science and Technology
dc.description.sponsorNational Science Foundation (U.S.). Division of Chemistry
dc.description.sponsorPennsylvania. Department of Health
dc.creator.orcid0000-0001-6885-2021
dc.temple.creatorBecica, Joseph
dc.temple.creatorDobereiner, Graham E.
refterms.dateFOA2020-04-22T14:17:23Z


Files in this item

Thumbnail
Name:
Dobereiner-PrePrint-2019-06.pdf
Size:
686.8Kb
Format:
PDF
Thumbnail
Name:
Dobereiner-PrePrint-2019-06-Su ...
Size:
19.03Mb
Format:
PDF
Description:
Supporting Information

This item appears in the following Collection(s)

Show simple item record

Attribution-NonCommercial-NoDerivs CC BY-NC-ND
Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs CC BY-NC-ND