{"doi":"10.1039/d4sc08637f","title":"Mechanistic insights into the regiodivergent insertion of bicyclo[1.1.0]butanes towards carbocycle-tethered N-heteroarenes","abstract":"Ring scaffolds constitute important sub-structures in nature and across the chemical industries. However, their straight-forward introduction into a target molecule or cross-linkage between cyclic motifs of choice comprise major challenges for methodology development. Herein, the interconnection of two prominent representatives of the 2D and 3D cyclic chemical space-namely N-heteroarenes and unsaturated carbocycles-in the form of hybrid cyclobutane-tethered N-heteroarenes is targeted. The diastereoselective introduction of decorated cyclobutanes is promoted by the insertion of strained bicyclo[1.1.0]butanes (BCBs) into the C-S bond of C2-thioether aza-arenes. In-depth density functional theory (DFT) studies provide insights on the key factors governing the unexpected regiodivergent insertion outcomes. A broad scope of mono- and bicyclic aza-arenes along with mono- and disubstituted BCBs are shown to be competent. Detailed mechanistic studies support an oxidative activation of the N-heteroarenes.","journal":"Chemical Science","year":2025,"id":515571,"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":13,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9528,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"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":1209245,"name":"Madina Lenz","orcid":null,"position":1,"is_corresponding":false},{"id":1201261,"name":"Poulami Mukherjee","orcid":"0000-0002-2876-7612","position":2,"is_corresponding":false},{"id":1379895,"name":"Yan-Bo Li","orcid":"0000-0002-7117-445X","position":3,"is_corresponding":false},{"id":1209246,"name":"Adhya Suresh","orcid":null,"position":4,"is_corresponding":false},{"id":408852,"name":"Constantin G. Daniliuc","orcid":"0000-0002-6709-3673","position":5,"is_corresponding":false},{"id":348357,"name":"Osvaldo Gutiérrez","orcid":"0000-0001-8151-7519","position":6,"is_corresponding":false},{"id":620631,"name":"Frank Glorius","orcid":"0000-0002-0648-956X","position":7,"is_corresponding":false},{"id":1379894,"name":"Johannes E. Erchinger","orcid":"0000-0001-6544-7282","position":0,"is_corresponding":true}],"reference_count":56,"raw_metadata":null,"created_at":"2026-07-19T02:48:39.436300Z","pmid":"39906383","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":[]}