{"doi":"10.1021/jacs.1c07117","title":"Copper-Catalyzed Cross-Coupling of Benzylic C–H Bonds and Azoles with Controlled <i>N</i>-Site Selectivity","abstract":"Azoles are important motifs in medicinal chemistry, and elaboration of their structures via direct N–H/C–H coupling could have broad utility in drug discovery. The ambident reactivity of many azoles, however, presents significant selectivity challenges. Here, we report a copper-catalyzed method that achieves site-selective cross-coupling of pyrazoles and other N–H heterocycles with substrates bearing (hetero)benzylic C–H bonds. Excellent N-site selectivity is achieved, with the preferred site controlled by the identity of co-catalytic additives. This cross-coupling strategy features broad scope for both the N–H heterocycle and benzylic C–H coupling partners, enabling application of this method to complex molecule synthesis and medicinal chemistry.","journal":"Journal of the American Chemical Society","year":2021,"id":151467,"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":83,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9526,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2021-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":279590,"name":"Dung L. Golden","orcid":"0000-0002-9044-4873","position":1,"is_corresponding":false},{"id":246772,"name":"Shane W. Krska","orcid":"0000-0001-9757-9036","position":2,"is_corresponding":false},{"id":110277,"name":"Shannon S. Stahl","orcid":"0000-0002-9000-7665","position":3,"is_corresponding":false},{"id":246768,"name":"Si-Jie Chen","orcid":"0000-0001-9836-6892","position":0,"is_corresponding":true}],"reference_count":57,"raw_metadata":null,"created_at":"2026-07-18T23:43:16.823357Z","pmid":"34464528","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":[]}