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With substrates containing both an amino group and a vinyl moiety, control of C\u2500N versus C\u2500C reactivity can lead to regiodivergent functionalizations. With this focus, reactions of silyl\u2010protected 8\u2010vinyl 2'\u2010deoxyadenosine and adenosine with aryl bromides and iodides have been studied. Pd(OAc)<jats:sub>2<\/jats:sub>, Pd<jats:sub>2<\/jats:sub>(dba)<jats:sub>3<\/jats:sub>, and preformed dichloro[1,1\u2032\u2010bis(di\u2010<jats:italic>t<\/jats:italic>\u2010butylphosphino)ferrocene]palladium (II) (Pd\u2010118) were evaluated as metal sources. Ligands tested were Xantphos, DPEphos, BIPHEP, and DPPF, with Cs<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub> and K<jats:sub>3<\/jats:sub>PO<jats:sub>4<\/jats:sub> as bases. In toluene as solvent, the Pd(OAc)<jats:sub>2<\/jats:sub>\/Xantphos\/Cs<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub> combination was uniquely capable of predominant <jats:italic>N<\/jats:italic><jats:sup>6<\/jats:sup> arylation. Aryl bromides and iodides gave comparable product yields. Replacement of Cs<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub> with K<jats:sub>3<\/jats:sub>PO<jats:sub>4<\/jats:sub> redirected arylation from the nitrogen atom to the vinyl carbon atom, and all other catalyst, ligand, and base combinations gave C<jats:sup>vinyl<\/jats:sup> arylation as well. Simply switching from Pd(OAc)<jats:sub>2<\/jats:sub> to Pd<jats:sub>2<\/jats:sub>(dba)<jats:sub>3<\/jats:sub> resulted in loss of the <jats:italic>N<\/jats:italic><jats:sup>6<\/jats:sup>\u2010selectivity and C<jats:sup>vinyl<\/jats:sup> arylation was favored. Based upon these results, using two structurally similar catalytic systems sequential C<jats:sup>vinyl<\/jats:sup> and <jats:italic>N<\/jats:italic><jats:sup>6<\/jats:sup> arylations of the nucleosides were accomplished. Some of the products were converted to other novel nucleoside analogues. Because some compounds were fluorescent, their photophysical properties were assessed experimentally and computationally.<\/jats:p>","DOI":"10.1002\/chem.202501477","type":"journal-article","created":{"date-parts":[[2025,7,3]],"date-time":"2025-07-03T22:13:27Z","timestamp":1751580807000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Pd\u2010Catalyzed Regiodivergent <i>N<\/i><sup>6<\/sup> versus C<sup>vinyl<\/sup> Arylation of 8\u2010Vinyl Adenine Nucleosides, Sequential Diarylation, Fluorescence Properties, and Computational Evaluations**"],"prefix":"10.1002","volume":"31","author":[{"given":"Hari K.","family":"Akula","sequence":"first","affiliation":[{"name":"Department of Chemistry and Biochemistry The City College of New York  160 Convent Avenue New York New York 10031 USA"},{"name":"The Ph.D. Program in Chemistry The Graduate Center of the City University of New York  New York New York 10016 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2021-4589","authenticated-orcid":false,"given":"Goutam","family":"Ghosh","sequence":"additional","affiliation":[{"name":"Department of Chemistry Brooklyn College  2900 Bedford Avenue Brooklyn NY 11210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4444-9099","authenticated-orcid":false,"given":"Alexander","family":"Greer","sequence":"additional","affiliation":[{"name":"The Ph.D. Program in Chemistry The Graduate Center of the City University of New York  New York New York 10016 USA"},{"name":"Department of Chemistry Brooklyn College  2900 Bedford Avenue Brooklyn NY 11210 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Padmanava","family":"Pradhan","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The City College of New York  160 Convent Avenue New York New York 10031 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9555-027X","authenticated-orcid":false,"given":"Mahesh K.","family":"Lakshman","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry The City College of New York  160 Convent Avenue New York New York 10031 USA"},{"name":"The Ph.D. Program in Chemistry The Graduate Center of the City University of New York  New York New York 10016 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,31]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1983.927"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00092a058"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199513481"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)00605-C"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature07369"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00512"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900587"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505268"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200404216"},{"key":"e_1_2_8_10_1","first-page":"107","volume-title":"Modern Arene Chemistry","author":"Hartwig J. 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