{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["He Q"],"funding":["NCI NIH HHS"],"pagination":["52-7"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4618486"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["92"],"pubmed_abstract":["An electrochemical method with the ability to conduct (18)F-fluorination of aromatic molecules through direct nucleophilic fluorination of cationic intermediates is presented in this paper. The reaction was performed on a remote-controlled automatic platform. Nucleophilic electrochemical fluorination of tert-butyloxycarbonyl (Boc) protected catechol, an intermediate model molecule for the positron emission tomography (PET) probe (3,4-dihydroxy-6-[(18)F]fluoro-L-phenylalanine), was performed. Fluorination was achieved under potentiostatic anodic oxidation in acetonitrile containing Et3N·3HF and other supporting electrolytes. Radiofluorination efficiency was influenced by a number of variables, including the concentration of the precursor, concentration of Et3N·3HF, type of supporting electrolyte, temperature and time, as well as applied potentials. Radio-fluorination efficiency of 10.4±0.6% (n=4) and specific activity of up to 43GBq/mmol was obtained after 1h electrolysis of 0.1M of 4-tert-butyl-diboc-catechol in the acetonitrile solution of Et3N·3HF (0.033M) and NBu4PF6 (0.05M). Density functional theory (DFT) was employed to explain the tert-butyl functional group facilitation of electrochemical oxidation and subsequent fluorination."],"journal":["Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine"],"pubmed_title":["Electrochemical nucleophilic synthesis of di-tert-butyl-(4-[18F]fluoro-1,2-phenylene)-dicarbonate."],"pmcid":["PMC4618486"],"funding_grant_id":["U54 CA151819"],"pubmed_authors":["Sadeghi S","Alfeazi I","He Q","Wang Y"],"additional_accession":[]},"is_claimable":false,"name":"Electrochemical nucleophilic synthesis of di-tert-butyl-(4-[18F]fluoro-1,2-phenylene)-dicarbonate.","description":"An electrochemical method with the ability to conduct (18)F-fluorination of aromatic molecules through direct nucleophilic fluorination of cationic intermediates is presented in this paper. The reaction was performed on a remote-controlled automatic platform. Nucleophilic electrochemical fluorination of tert-butyloxycarbonyl (Boc) protected catechol, an intermediate model molecule for the positron emission tomography (PET) probe (3,4-dihydroxy-6-[(18)F]fluoro-L-phenylalanine), was performed. Fluorination was achieved under potentiostatic anodic oxidation in acetonitrile containing Et3N·3HF and other supporting electrolytes. Radiofluorination efficiency was influenced by a number of variables, including the concentration of the precursor, concentration of Et3N·3HF, type of supporting electrolyte, temperature and time, as well as applied potentials. Radio-fluorination efficiency of 10.4±0.6% (n=4) and specific activity of up to 43GBq/mmol was obtained after 1h electrolysis of 0.1M of 4-tert-butyl-diboc-catechol in the acetonitrile solution of Et3N·3HF (0.033M) and NBu4PF6 (0.05M). Density functional theory (DFT) was employed to explain the tert-butyl functional group facilitation of electrochemical oxidation and subsequent fluorination.","dates":{"release":"2014-01-01T00:00:00Z","publication":"2014 Sep","modification":"2024-11-15T15:06:41.464Z","creation":"2019-03-27T02:00:42Z"},"accession":"S-EPMC4618486","cross_references":{"pubmed":["25000498"],"doi":["10.1016/j.apradiso.2014.06.013"]}}