{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Joshi C"],"funding":["NIGMS NIH HHS","NIH HHS"],"pagination":["2959-2966"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10168682"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["12(5)"],"pubmed_abstract":["Experimental and theoretical <sup>13</sup>C kinetic isotope effects (KIEs) are utilized to obtain atomistic insight into the catalytic mechanism of the Pd(PPh<sub>3</sub>)<sub>4</sub>-catalyzed Suzuki-Miyaura reaction of aryl halides and aryl boronic acids. Under catalytic conditions, we establish that oxidative addition of aryl bromides occurs to a 12-electron monoligated palladium complex (Pd-(PPh<sub>3</sub>)). This is based on the congruence of the experimental KIE for the carbon attached to bromine (KIE<sub>C-Br</sub> = 1.020) and predicted KIE<sub>C-Br</sub> for the transition state for oxidative addition to the Pd(PPh<sub>3</sub>) complex (1.021). For aryl iodides, the near-unity KIE<sub>C-I</sub> of ~1.003 suggests that the first irreversible step in the catalytic cycle precedes ox"],"journal":["ACS catalysis"],"pubmed_title":["Isotope Effects Reveal the Catalytic Mechanism of the Archetypical Suzuki-Miyaura Reaction."],"pmcid":["PMC10168682"],"funding_grant_id":["S10 OD026746","R01 GM126283"],"pubmed_authors":["Kim S","Izzo JA","Hirschi JS","Macharia JM","Vetticatt MJ","Joshi C","Wambua V"],"additional_accession":[]},"is_claimable":false,"name":"Isotope Effects Reveal the Catalytic Mechanism of the Archetypical Suzuki-Miyaura Reaction.","description":"Experimental and theoretical <sup>13</sup>C kinetic isotope effects (KIEs) are utilized to obtain atomistic insight into the catalytic mechanism of the Pd(PPh<sub>3</sub>)<sub>4</sub>-catalyzed Suzuki-Miyaura reaction of aryl halides and aryl boronic acids. Under catalytic conditions, we establish that oxidative addition of aryl bromides occurs to a 12-electron monoligated palladium complex (Pd-(PPh<sub>3</sub>)). This is based on the congruence of the experimental KIE for the carbon attached to bromine (KIE<sub>C-Br</sub> = 1.020) and predicted KIE<sub>C-Br</sub> for the transition state for oxidative addition to the Pd(PPh<sub>3</sub>) complex (1.021). For aryl iodides, the near-unity KIE<sub>C-I</sub> of ~1.003 suggests that the first irreversible step in the catalytic cycle precedes ox","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Mar","modification":"2025-04-18T13:57:23.318Z","creation":"2025-04-06T23:50:06.924Z"},"accession":"S-EPMC10168682","cross_references":{"pubmed":["37168650"],"doi":["10.1021/acscatal.1c05802"]}}