{"doi":"10.1002/ejoc.201901784","title":"Selectivity in the Addition of Electron‐Deficient Radicals to the <i>C</i>2 Position of Indoles","abstract":"The addition of electron‐deficient radicals to the C2 position of indoles has been described in the literature as opposed to electrophilic addition at the C 3 position. Density functional theory calculations were used to understand the switch in regioselectivity from C3 to C2 for indole to undergo radical additions. Electron deficient radicals have a lower barrier for the reaction at C 2 and a lower energy radical intermediate that benefits from benzylic radical stabilization. Trifluoromethyl radical addition has a lower energy barrier than acetonitrile radical, and the C 3 addition transition state is just 0.8 kcal/mol higher than C2 . This is supported by experimental observations.","journal":"European Journal of Organic Chemistry","year":2020,"id":77504,"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":19,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9527,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2020-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":403980,"name":"Roy J. Vaz","orcid":"0000-0001-5446-4343","position":1,"is_corresponding":false},{"id":403981,"name":"Steven H. Olson","orcid":"0000-0001-9615-9355","position":2,"is_corresponding":false},{"id":403982,"name":"Mark Munson","orcid":"0000-0001-8632-1144","position":3,"is_corresponding":false},{"id":5843,"name":"Nick A. Paras","orcid":"0000-0001-5742-4056","position":4,"is_corresponding":false},{"id":5844,"name":"Jay C. Conrad","orcid":"0000-0002-9048-8833","position":5,"is_corresponding":false},{"id":403979,"name":"Yi Li","orcid":"0000-0002-4236-262X","position":0,"is_corresponding":true}],"reference_count":37,"raw_metadata":null,"created_at":"2026-07-18T21:49:16.197289Z","pmid":"33692651","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":[]}