{"doi":"10.1021/jacs.9b05461","title":"LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates","abstract":null,"journal":"Journal of the American Chemical Society","year":2019,"id":688020,"datarank":0.8137425026222106,"base_score":5.424950017481403,"endowment":5.424950017481403,"self_citation_contribution":0.8137425026222106,"citation_network_contribution":0.0,"self_endowment_contribution":0.8137425026222106,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":226,"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":1022702,"name":"Laura K. G. Ackerman","orcid":"0000-0002-7189-1213","position":1,"is_corresponding":false},{"id":1098794,"name":"Kai Kang","orcid":"0000-0001-7936-8569","position":2,"is_corresponding":false},{"id":1797396,"name":"Astrid M. Parsons","orcid":"0000-0002-3835-9110","position":3,"is_corresponding":false},{"id":247427,"name":"Daniel J. Weix","orcid":"0000-0002-9552-3378","position":4,"is_corresponding":false},{"id":270386,"name":"Liangbin Huang","orcid":"0000-0001-9450-9454","position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates","abstract":"While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy with the appropriate choice of additive. Studies demonstrate that LiCl is essential for effective cross-coupling by accelerating the reduction of Ni(II) to Ni(0) and counteracting autoinhibition of reduction at Zn(0) by Zn(II) salts. The modified conditions tolerate a variety of functional groups on either coupling partner (42 examples), and examples include a three-step synthesis of flurbiprofen.","is_dataset_classified":null,"base_score":5.424950017481403,"endowment":5.424950017481403,"datacite_reuse_total":0,"file_count":0,"downloads":0,"views":0,"has_version_chain":false,"is_dataset":false,"is_oa":false,"pmid":"31257881","pmcid":"PMC6685420","openalex_id":"https://openalex.org/W2954845784","authors":[],"funders":[{"funder_name":"Division of Graduate Education","grant_id":"DGE-1419118","title":null},{"funder_name":"National Institute of General Medical Sciences","grant_id":"R01GM097243","title":null},{"funder_name":"National Science Foundation","grant_id":"1419118","title":"Graduate Research Fellowship Program (GRFP)"},{"funder_name":"National Institutes of Health","grant_id":"5R01GM097243-14","title":"Mechanistically Guided Cross-Electrophile Coupling Approaches to Useful Csp2-Csp2 and Csp2- Csp3 Bonds"},{"funder_name":"Novartis","grant_id":"","title":null},{"funder_name":"Boehringer Ingelheim","grant_id":"","title":null},{"funder_name":"Camille and Henry Dreyfus Foundation","grant_id":"","title":null},{"funder_name":"Shanghai Institute of Organic Chemistry","grant_id":"","title":null}],"total_grants":8,"fwci":11.0792,"citation_percentile":0.99375509,"influential_citations":0,"citation_trend":[{"year":2019,"count":5},{"year":2020,"count":32},{"year":2021,"count":39},{"year":2022,"count":34},{"year":2023,"count":41},{"year":2024,"count":32},{"year":2025,"count":28},{"year":2026,"count":15}],"oa_status":"hybrid","license":"cc-by-nc-nd","oa_locations":[{"url":"https://doi.org/10.1021/jacs.9b05461","host_type":"journal"},{"url":"https://doi.org/10.1021/jacs.9b05461","host_type":"publisher"},{"url":"http://pubs.acs.org/doi/pdf/10.1021/jacs.9b05461","host_type":"publisher"},{"url":"https://pubs.acs.org/doi/pdf/10.1021/jacs.9b05461","host_type":"publisher"},{"url":"https://pubmed.ncbi.nlm.nih.gov/31257881","host_type":"repository"},{"url":"https://www.ncbi.nlm.nih.gov/pmc/articles/6685420","host_type":"repository"},{"url":"https://europepmc.org/articles/PMC6685420","host_type":"Europe_PMC"},{"url":"https://europepmc.org/articles/PMC6685420?pdf=render","host_type":"Europe_PMC"},{"url":"http://dx.doi.org/10.1021/jacs.9b05461","host_type":""},{"url":"https://dx.doi.org/10.1021/jacs.9b05461","host_type":""}],"fields_of_study":["Catalytic Cross-Coupling Reactions","Catalytic C–H Functionalization Methods","Coordination Chemistry and Organometallics","01 natural sciences","0104 chemical sciences","Coordination Complexes","Hydrocarbons, Chlorinated","Lithium Chloride","Mesylates","Molecular Structure","Nickel","Zinc"],"mesh_terms":["Hydrocarbons, Chlorinated","Mesylates","Nickel","Zinc","Molecular Structure","Lithium Chloride","Coordination Complexes"],"keywords":["Electrophile","Aryl","Chemistry","Combinatorial chemistry","Coupling reaction","Coupling (piping)","Medicinal chemistry","Organic chemistry","Catalysis","Alkyl","Mesylates","Zinc","Molecular Structure","Coordination Complexes","Nickel","Hydrocarbons, Chlorinated","Lithium Chloride"],"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":"2026-08-19T12:14:42.098227Z","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":[]}