{"doi":"10.3390/molecules25092128","title":"Conjugate Addition of Grignard Reagents to Thiochromones Catalyzed by Copper Salts: A Unified Approach to Both 2-Alkylthiochroman-4-One and Thioflavanone","abstract":"Grignard reagents undergo conjugate addition to thiochromones catalyzed by copper salts to afford 2-substituted-thiochroman-4-ones, both 2-alkylthiochroman-4-ones and thioflavanones (2-arylthiochroman-4-ones), in good yields with trimethylsilyl chloride (TMSCl) as an additive. The best yields of 1,4-adducts can be attained with CuCN∙2LiCl as the copper source. Excellent yields of 2-alkyl-substituted thiochroman-4-ones and thioflavanones (2-aryl substituted) are attained with a broad range of Grignard reagents. This approach works well with both alkyl and aromatic Grignard reagents, thus providing a unified synthetic approach to privileged 2-substituted thiochroman-4-ones and a potential valuable precursor for further synthetic applications towards many pharmaceutically active molecules. The use of commercially available and/or readily prepared Grignard reagents will expedite the synthesis of a large library of both 2-alkyl substituted thiochroman-4-ones and thioflavanones for additional synthetic applications.","journal":"Molecules","year":2020,"id":84903,"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":8,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9487,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2020-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":435270,"name":"Teavian Harvin","orcid":null,"position":1,"is_corresponding":false},{"id":435271,"name":"Ti’Bran Pickens-Flynn","orcid":null,"position":2,"is_corresponding":false},{"id":435272,"name":"Nataleigh Austin","orcid":null,"position":3,"is_corresponding":false},{"id":435273,"name":"Samuel H. Whitaker","orcid":null,"position":4,"is_corresponding":false},{"id":435274,"name":"Mai Ling C. Tang Yuk Tutein","orcid":null,"position":5,"is_corresponding":false},{"id":435275,"name":"Dabria T. Hukins","orcid":null,"position":6,"is_corresponding":false},{"id":435276,"name":"Nichele Deese","orcid":null,"position":7,"is_corresponding":false},{"id":434643,"name":"Fenghai Guo","orcid":"0000-0001-9099-0965","position":8,"is_corresponding":false},{"id":434642,"name":"Tania J. Bellinger","orcid":"0000-0001-9388-8958","position":0,"is_corresponding":true}],"reference_count":72,"raw_metadata":null,"created_at":"2026-07-18T21:55:38.506333Z","pmid":"32370080","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":[]}