{"doi":"10.1021/acs.joc.3c00917","title":"Practical Synthesis of Terminal Vinyl Fluorides","abstract":"The synthesis of di- and trisubstituted vinyl fluorides with high isomeric purity remains a challenge for organic synthesis. While many methods exist to access these compounds, the separation of the desired isomer from the minor isomer and/or starting materials often is difficult. Herein, we report a practical method to access di- and trisubstituted vinyl fluorides via a selective Horner–Wadsworth–Emmons olefination/hydrolysis, which provides crystalline 2-fluoroacrylic acids in high (>98%) E -isomeric purity. A subsequent silver-catalyzed stereoretentive decarboxylation provides the title substances with high isomeric purity and without the need for tedious chromatography to remove the minor isomer. The process was amenable to a variety of aldehydes and ketones and provided a diverse array of di- and trisubstituted vinyl fluorides. The sequence was applied to the synthesis of antibacterial and anti-inflammatory compounds.","journal":"The Journal of Organic Chemistry","year":2023,"id":364204,"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":7,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9435,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2023-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":537785,"name":"Brent V. Powell","orcid":"0000-0003-2264-8134","position":1,"is_corresponding":false},{"id":578454,"name":"Olga V. Zatolochnaya","orcid":"0000-0003-3680-2913","position":2,"is_corresponding":false},{"id":1118997,"name":"Joyce C. Leung","orcid":"0000-0003-2246-1599","position":3,"is_corresponding":false},{"id":1119437,"name":"Scott Pennino","orcid":null,"position":4,"is_corresponding":false},{"id":1119438,"name":"Lifen Wu","orcid":null,"position":5,"is_corresponding":false},{"id":1118998,"name":"Nina C. Gonnella","orcid":"0000-0001-8944-7180","position":6,"is_corresponding":false},{"id":1118999,"name":"Bangaru Bhaskararao","orcid":"0000-0003-1618-0707","position":7,"is_corresponding":false},{"id":325869,"name":"Marisa C. Kozlowski","orcid":"0000-0002-4225-7125","position":8,"is_corresponding":false},{"id":96010,"name":"Jonathan T. Reeves","orcid":"0000-0002-3051-3304","position":9,"is_corresponding":false},{"id":1118996,"name":"И. С. Волчков","orcid":"0000-0002-4578-6380","position":0,"is_corresponding":true}],"reference_count":59,"raw_metadata":null,"created_at":"2026-07-19T01:14:36.728255Z","pmid":"37441763","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":[]}