{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Lalloo N"],"funding":["National Institute of General Medical Sciences","NIGMS NIH HHS"],"pagination":["18617-18625"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8693446"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["143(44)"],"pubmed_abstract":["This Article describes the development of a decarbonylative Pd-catalyzed aryl-fluoroalkyl bond-forming reaction that couples fluoroalkylcarboxylic acid-derived electrophiles [R<sub>F</sub>C(O)X] with aryl organometallics (Ar-M'). This reaction was optimized by interrogating the individual steps of the catalytic cycle (oxidative addition, carbonyl de-insertion, transmetalation, and reductive elimination) to identify a compatible pair of coupling partners and an appropriate Pd catalyst. These stoichiometric organometallic studies revealed several critical elements for reaction design. First, uncatalyzed background reactions between R<sub>F</sub>C(O)X and Ar-M' can be avoided by using M' = boronate ester. Second, carbonyl de-insertion and Ar-R<sub>F</sub> reductive elimination are the two slo"],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis."],"pmcid":["PMC8693446"],"funding_grant_id":["R35 GM136332","R35GM1361332"],"pubmed_authors":["Malapit CA","Sanford MS","Lalloo N","Taimoory SM","Brigham CE"],"additional_accession":[]},"is_claimable":false,"name":"Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.","description":"This Article describes the development of a decarbonylative Pd-catalyzed aryl-fluoroalkyl bond-forming reaction that couples fluoroalkylcarboxylic acid-derived electrophiles [R<sub>F</sub>C(O)X] with aryl organometallics (Ar-M'). This reaction was optimized by interrogating the individual steps of the catalytic cycle (oxidative addition, carbonyl de-insertion, transmetalation, and reductive elimination) to identify a compatible pair of coupling partners and an appropriate Pd catalyst. These stoichiometric organometallic studies revealed several critical elements for reaction design. First, uncatalyzed background reactions between R<sub>F</sub>C(O)X and Ar-M' can be avoided by using M' = boronate ester. Second, carbonyl de-insertion and Ar-R<sub>F</sub> reductive elimination are the two slo","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 Nov","modification":"2025-04-04T09:02:59.667Z","creation":"2025-04-04T09:02:59.667Z"},"accession":"S-EPMC8693446","cross_references":{"pubmed":["34709804"],"doi":["10.1021/jacs.1c08551"]}}