{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Stephens DE"],"funding":["Ministerio de Economía y Finanzas, Panamá","NCRR NIH HHS","Instituto para la Formación y Aprovechamiento de Recursos Humanos","NIMHD NIH HHS","Welch Foundation","National Institute of General Medical Sciences","NIGMS NIH HHS","Max and Minnie Tomerlin Voelcker Fund"],"pagination":["167-175"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4286811"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["5(1)"],"pubmed_abstract":["We report herein a palladium-catalyzed C-H arylation of quinoline <i>N</i>-oxides that proceeds with high selectivity in favor of the C8-isomer. This site-selectivity is unusual for palladium, since all of the hitherto described methods of palladium-catalyzed C-H functionalization of quinoline <i>N</i>-oxides are highly C2-selective. The reaction exhibits a broad synthetic scope with respect to quinoline <i>N</i>-oxides and iodoarenes and can be significantly accelerated to sub-hour reaction times under microwave irradiation. The C8-arylation method can be carried out on gram scale and has excellent functional group tolerance. Mechanistic and Density Functional Theory (DFT) computational studies provide evidence for the cyclopalladation pathway and describe key parameters influencing the s"],"journal":["ACS catalysis"],"pubmed_title":["Palladium-Catalyzed C8-Selective C-H Arylation of Quinoline <i>N</i>-Oxides: Insights into the Electronic, Steric and Solvation Effects on the Site-Selectivity by Mechanistic and DFT Computational Studies."],"pmcid":["PMC4286811"],"funding_grant_id":["SC3GM105579","SC3 GM105579","AX-1788","DIPRENA-DPIP-10866-2013","G12 RR013646","SC3 GM109853","G12 MD007591"],"pubmed_authors":["Atesin TA","Stephens DE","Atesin AC","Lakey-Beitia J","Chavez G","Larionov OV","Arman HD"],"additional_accession":[]},"is_claimable":false,"name":"Palladium-Catalyzed C8-Selective C-H Arylation of Quinoline <i>N</i>-Oxides: Insights into the Electronic, Steric and Solvation Effects on the Site-Selectivity by Mechanistic and DFT Computational Studies.","description":"We report herein a palladium-catalyzed C-H arylation of quinoline <i>N</i>-oxides that proceeds with high selectivity in favor of the C8-isomer. This site-selectivity is unusual for palladium, since all of the hitherto described methods of palladium-catalyzed C-H functionalization of quinoline <i>N</i>-oxides are highly C2-selective. The reaction exhibits a broad synthetic scope with respect to quinoline <i>N</i>-oxides and iodoarenes and can be significantly accelerated to sub-hour reaction times under microwave irradiation. The C8-arylation method can be carried out on gram scale and has excellent functional group tolerance. Mechanistic and Density Functional Theory (DFT) computational studies provide evidence for the cyclopalladation pathway and describe key parameters influencing the s","dates":{"release":"2015-01-01T00:00:00Z","publication":"2015 Jan","modification":"2026-04-13T08:48:37.141Z","creation":"2019-03-27T01:42:55Z"},"accession":"S-EPMC4286811","cross_references":{"pubmed":["25580364"],"doi":["10.1021/cs501813v"]}}