{"doi":"10.1039/d4sc04885g","title":"Modular synthesis of aryl amines from 3-alkynyl-2-pyrones","abstract":"The synthesis of aryl amines from 3-alkynyl-2-pyrones and various amines is described. Mechanistically, the aryl amines are proposed to arise from the 3-alkynyl-2-pyrone substrates through their selective opening in a 1,6-fashion by secondary amines followed by decarboxylation and an unexpected rearrangement. The proposed mechanism is supported by quantum chemical transition-state calculations, which are consistent with the regiochemical outcome. The scope of this transformation spans a variety of 3-alkynyl-2-pyrones and a range of secondary amines. The influence of the secondary amine coupling partners on reaction efficiency was elucidated through data-driven modeling as well as scope exploration. These latter studies revealed that the steric bulk of the secondary amine coupling partner under the reaction conditions serves as a strong indicator of overall reaction efficiency.","journal":"Chemical Science","year":2024,"id":456418,"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":6,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9451,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2024-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":700822,"name":"Louis de Lescure","orcid":"0000-0002-5777-3771","position":1,"is_corresponding":false},{"id":1071846,"name":"Melissa A. Hardy","orcid":"0000-0002-3924-4518","position":2,"is_corresponding":false},{"id":1280833,"name":"Jin Tan","orcid":"0000-0001-8409-1672","position":3,"is_corresponding":false},{"id":308530,"name":"Matthew S. Sigman","orcid":"0000-0002-5746-8830","position":4,"is_corresponding":false},{"id":700824,"name":"Robert S. Paton","orcid":"0000-0002-0104-4166","position":5,"is_corresponding":false},{"id":308347,"name":"Richmond Sarpong","orcid":"0000-0002-0028-6323","position":6,"is_corresponding":false},{"id":495631,"name":"Kristen E. Gardner","orcid":"0000-0002-6712-7001","position":0,"is_corresponding":true}],"reference_count":30,"raw_metadata":null,"created_at":"2026-07-19T02:03:27.785212Z","pmid":"39246374","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":[]}