{"doi":"10.3762/bjoc.17.123","title":"Development of <i>N</i>-F fluorinating agents and their fluorinations: Historical perspective","abstract":"This review deals with the historical development of all N -F fluorinating agents developed so far. The unique properties of fluorine make fluorinated organic compounds attractive in many research areas and therefore fluorinating agents are important. N -F agents have proven useful by virtue of their easy handling. This reagent class includes many types of N -F compounds: perfluoro- N -fluoropiperidine, N -fluoro-2-pyridone, N -fluoro- N -alkylarenesulfonamides, N -fluoropyridinium salts and derivatives, N -fluoroquinuclidium salts, N -fluoro-trifluoromethanesulfonimide, N -fluoro-sultams, N -fluoro-benzothiazole dioxides, N -fluoro-lactams, N -fluoro- o -benzenedisulfonimide, N -fluoro-benzenesulfonimide, 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, N -fluoropyridinium-2-sulfonate derivatives, 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane salts, N -fluorodinitroimidazole, N -fluoro-trichloro-1,3,5-triazinium salt, N -F ethano-Tröger’s base derivatives, N -fluoro-methanesulfonimide, N -fluoro- N -arylarenesulfonamides, bis N -F salts such as N , N’ -difluorobipyridinium salts and N , N’ -difluoro-1,4-diazoniabicyclo[2.2.2]octane salts, and their many derivatives and analogs, including chiral N -F reagents such as optically active N -fluoro-sultam derivatives, N -fluoro-alkaloid derivatives, DABCO-based N -F derivatives, and N -F binaphthyldisulfonimides. The synthesis and reactions of these reagents are described chronologically and the review also discusses the relative fluorination power of each reagent and their mechanisms chronicling developments from a historical perspective.","journal":"Beilstein Journal of Organic Chemistry","year":2021,"id":153755,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":67,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.951,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2021-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":353817,"name":"Yuhao Yang","orcid":"0000-0003-1952-5547","position":1,"is_corresponding":false},{"id":353818,"name":"Gerald B. Hammond","orcid":"0000-0002-9814-5536","position":2,"is_corresponding":false},{"id":651881,"name":"Teruo Umemoto","orcid":"0000-0002-8718-8127","position":0,"is_corresponding":true}],"reference_count":171,"raw_metadata":null,"created_at":"2026-07-18T23:43:44.759273Z","pmid":"34386101","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}