Show simple item record

dc.contributor.authorHumke, Jenna N.
dc.contributor.authorDaley, Ryan A.
dc.contributor.authorMorrenzin, Aaron S.
dc.contributor.authorNeufeldt, Sharon R.
dc.contributor.authorTopczewski, Joseph J.
dc.identifier.citationHumke, J. N., Daley, R. A., Morrenzin, A. S., Neufeldt, S. R., & Topczewski, J. J. (2021). Combined Experimental and Computational Mechanistic Investigation of the Palladium-Catalyzed Decarboxylative Cross-Coupling of Sodium Benzoates with Chloroarenes. The Journal of Organic Chemistry, 86(17), 11419-11433.en_US
dc.descriptionThis document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see
dc.description.abstractReported herein is a mechanistic investigation into the palladium catalyzed decarboxylative cross-coupling of sodium benzoates and chloroarenes. The reaction was found to be first order in Pd. A minimal substituent effect was observed with respect to the chloroarene and the reaction was zero order with respect to chloroarene. Palladium mediated decarboxylation was assigned as the turn-over limiting step based on an Eyring plot and DFT computations. Catalyst performance was found to vary based on the electrophile, which is best explained by catalyst decomposition at Pd(0). The COD ligand contained in the precatalyst CODPd(CH2TMS)2 (Pd1) was shown to be a beneficial additive. The bench stable Buchwald complex XPhos-PdG2 could be used with exogenous COD and XPhos instead of complex Pd1. Adding exogenous XPhos significantly increased the catalyst TON and enhanced reproducibility.en_US
dc.publisherAmerican Chemical Societyen_US
dc.rightscopyright The Journal of Organic Chemistry 2021en_US
dc.titleCombined Experimental and Computational Mechanistic Investigation of the Palladium-Catalyzed Decarboxylative Cross-Coupling of Sodium Benzoates with Chloroarenesen_US
mus.citation.journaltitleThe Journal of Organic Chemistryen_US
mus.relation.collegeCollege of Letters & Scienceen_US
mus.relation.departmentChemistry & Biochemistry.en_US
mus.relation.universityMontana State University - Bozemanen_US

Files in this item


This item appears in the following Collection(s)

Show simple item record

MSU uses DSpace software, copyright © 2002-2017  Duraspace. For library collections that are not accessible, we are committed to providing reasonable accommodations and timely access to users with disabilities. For assistance, please submit an accessibility request for library material.