{"doi":"10.1055/a-2714-9637","title":"C–F Bond Functionalization with Organolithium Compounds","abstract":"Abstract Cross-coupling of alkyl fluorides and organolithium compounds is achieved by liquid-assisted stirring and mild heating without the need for expensive catalysts or additives. The reaction proceeds with a variety of primary, secondary, and tertiary fluorides; several functional groups, including alkyl halides, ether, amide, and heteroaryl groups, are tolerated; and both aryl and alkyllithium compounds can be used. Mechanistic studies indicate that the reaction involves heterolytic C–F bond activation and proceeds either via generation of short-lived carbocation intermediates or through a concerted pathway, which probably predominates with primary substrates, while the formation of thermodynamically stable lithium fluoride is the driving force.","journal":"Synthesis","year":2025,"id":576545,"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":0,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9465,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2025-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1275922,"name":"D. Lucas Kane","orcid":"0000-0002-6681-3448","position":1,"is_corresponding":false},{"id":1275923,"name":"Bryan C. Figula","orcid":"0000-0003-3244-6077","position":2,"is_corresponding":false},{"id":1157767,"name":"Dea Xhili","orcid":null,"position":3,"is_corresponding":false},{"id":1384254,"name":"Grace E. Hana","orcid":null,"position":4,"is_corresponding":false},{"id":706664,"name":"Jeffery A. Bertke","orcid":"0000-0002-3419-5163","position":5,"is_corresponding":false},{"id":240835,"name":"Christian Wolf","orcid":"0000-0002-4447-3753","position":6,"is_corresponding":false},{"id":1383600,"name":"Maria Bouda","orcid":"0000-0001-9946-1218","position":0,"is_corresponding":true}],"reference_count":64,"raw_metadata":null,"created_at":"2026-07-19T02:57:56.636458Z","pmid":null,"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":[]}