High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides
dc.creator | Becica, Joseph | |
dc.creator | Hruszkewycz, Damian | |
dc.creator | Steves, Janelle | |
dc.creator | Elward, Jennifer | |
dc.creator | Leitch, David | |
dc.creator | Dobereiner, Graham | |
dc.date.accessioned | 2020-04-22T14:17:23Z | |
dc.date.available | 2020-04-22T14:17:23Z | |
dc.date.issued | 2019-06-09 | |
dc.identifier.citation | Becica, 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.doi | http://dx.doi.org/10.34944/dspace/50 | |
dc.identifier.uri | http://hdl.handle.net/20.500.12613/63 | |
dc.description.abstract | Sulfonamides 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.extent | 6 pages | |
dc.language | English | |
dc.language.iso | eng | |
dc.relation.ispartof | Faculty/ Researcher Works | |
dc.relation.isreferencedby | ChemRxiv | |
dc.rights | Attribution-NonCommercial-NoDerivs CC BY-NC-ND | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.subject | Sulfonamides | |
dc.subject | Heterocycles | |
dc.subject | Palladium | |
dc.subject | Phosphine parameterization | |
dc.subject | High throughput experimentation | |
dc.title | High-Throughput Discovery and Evaluation of a General Catalytic Method for N-Arylation of Weakly Nucleophilic Sulfonamides | |
dc.type | Text | |
dc.type.genre | Pre-print | |
dc.description.department | Chemistry | |
dc.relation.doi | https://doi.org/10.26434/chemrxiv.9108461.v2 | |
dc.ada.note | For Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu | |
dc.description.schoolcollege | Temple University. College of Science and Technology | |
dc.description.sponsor | National Science Foundation (U.S.). Division of Chemistry | |
dc.description.sponsor | Pennsylvania. Department of Health | |
dc.creator.orcid | 0000-0001-6885-2021 | |
dc.temple.creator | Becica, Joseph | |
dc.temple.creator | Dobereiner, Graham E. | |
refterms.dateFOA | 2020-04-22T14:17:23Z |