{"doi":"10.1021/om1005726","title":"Unexpected C<sub>carbene</sub>−X (X: I, Br, Cl) Reductive Elimination from N-Heterocyclic Carbene Copper Halide Complexes Under Oxidative Conditions","abstract":null,"journal":"Organometallics","year":2010,"id":676989,"datarank":0.5333022092234121,"base_score":3.5553480614894135,"endowment":3.5553480614894135,"self_citation_contribution":0.5333022092234121,"citation_network_contribution":0.0,"self_endowment_contribution":0.5333022092234121,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":34,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":971396,"name":"Peng Kang","orcid":"0000-0002-6639-8299","position":1,"is_corresponding":false},{"id":971400,"name":"T. Daniel P. Stack","orcid":"0000-0002-2886-4068","position":2,"is_corresponding":false},{"id":1768820,"name":"Bo-Lin Lin","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Unexpected C<sub>carbene</sub>−X (X: I, Br, Cl) Reductive Elimination from N-Heterocyclic Carbene Copper Halide Complexes Under Oxidative Conditions","abstract":"The non-innocent behaviors of NHC ligands have attracted wide attention due to their important implications for catalyst designs and reaction mechanisms. Herein, we report facile C(carbene)-halogen reductive eliminations from NHC copper halide complexes at RT under oxidative conditions. Density functional calculations on a simplified model system suggest that the reactions occur through oxidation of Cu(I) to Cu(III) species followed by C(carbene)-halogen reductive eliminations from NHC Cu(III) halide complexes. Remarkably short C(carbene)-chloride contacts and rare interactions between the chloride lone pair electrons and the C(carbene)p(π) orbital were found for the calculated NHC Cu(III) chlorides. The facile C(carbene)-X reductive elimination reported here warrants consideration as a potential decomposition pathway in reactions involving NHC-supported high-valent metal complexes, especially with late transition metals.","is_dataset_classified":null,"base_score":3.5553480614894135,"endowment":3.5553480614894135,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"21116469","pmcid":"PMC2992331","openalex_id":"https://openalex.org/W2017495338","authors":[],"funders":[{"funder_name":"NIGMS NIH HHS","grant_id":"R29 GM050730","title":null},{"funder_name":"NIGMS NIH HHS","grant_id":"R01 GM050730","title":null}],"total_grants":2,"fwci":1.6726,"citation_percentile":0.8214266,"influential_citations":0,"citation_trend":[{"year":2012,"count":4},{"year":2013,"count":2},{"year":2014,"count":2},{"year":2015,"count":4},{"year":2016,"count":1},{"year":2017,"count":4},{"year":2018,"count":1},{"year":2019,"count":4},{"year":2020,"count":3},{"year":2021,"count":2},{"year":2022,"count":1},{"year":2023,"count":1},{"year":2025,"count":1}],"oa_status":"closed","license":null,"oa_locations":[{"url":"https://pubs.acs.org/doi/pdf/10.1021/om1005726","host_type":"publisher"},{"url":"https://doi.org/10.1021/om1005726","host_type":"journal"},{"url":"https://pubmed.ncbi.nlm.nih.gov/21116469","host_type":"repository"},{"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/2992331","host_type":"repository"}],"fields_of_study":["N-Heterocyclic Carbenes in Organic and Inorganic Chemistry","Catalytic Cross-Coupling Reactions","Catalytic C–H Functionalization Methods"],"mesh_terms":[],"keywords":["Chemistry","Carbene","Reductive elimination","Halide","Oxidative addition","Halogen","Lone pair","Medicinal chemistry","Catalysis","Transition metal","Copper","Decomposition","Chloride","Photochemistry","Inorganic chemistry","Organic chemistry","Molecule","Alkyl"],"sdg_mappings":[{"sdg_number":0,"sdg_label":"Clean water and sanitation"}],"linked_datasets":[],"clinical_trials":[],"software_tools":[],"database_accessions":[],"source":"live","citation_network_status":"fetched"},"created_at":"2026-08-17T03:26:30.843492Z","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":[]}