{"id":"W2923350203","doi":"10.1021/acs.orglett.9b00591","title":"Dearomatization–Rearomatization Strategy for Reductive Cross-Coupling of Indoles with Ketones in Water","year":2019,"lang":"en","type":"article","venue":"Organic Letters","topic":"Catalytic C–H Functionalization Methods","field":"Chemistry","cited_by":48,"is_retracted":false,"has_abstract":true,"ca_institutions":"McGill University; Centre in Green Chemistry and Catalysis","funders":"Joint Research Centre; Natural Sciences and Engineering Research Council of Canada; Fundamental Research Funds for the Central Universities; Recruitment Program of Global Experts; Fonds Québécois de la Recherche sur la Nature et les Technologies; E.B. Eddy Endowment Fund; Ministry of Education of the People's Republic of China; Canada Research Chairs; Canada Foundation for Innovation; Science and Technology Department of Gansu Province; Lanzhou University","keywords":"Chemistry; Alkylation; Indole test; Steric effects; Nucleophile; Electrophile; Reagent; Nitrogen atom; Molecule; Combinatorial chemistry; Organic chemistry; Computational chemistry; Medicinal chemistry; Catalysis; Group (periodic table)","routes":{"ca_aff":true,"ca_fund":true,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":false},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"codex-gemma-dda1882f352a","candidate_categories":["insufficient_payload"],"consensus_categories":[],"category_scores_codex":[0.0002088047,0.0001388309,0.0002043853,0.0001045517,0.00004024787,0.00004247536,0.0001169542,0.00008239787,0.001169888],"category_scores_gemma":[0.00007818173,0.0001137177,0.00003473707,0.0002195415,0.00007038656,0.0002414789,0.00002553397,0.00007668602,0.00002006106],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0001146627,"about_ca_system_score_gemma":0.00005784234,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.00002261272,"about_ca_topic_score_gemma":0.000009075873,"domain_scores_codex":[0.998983,0.000008009347,0.0003370996,0.0002790899,0.0002077299,0.0001850402],"domain_scores_gemma":[0.999337,0.000122388,0.0001465985,0.0002373923,0.0001294438,0.00002717064],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"bench_or_experimental","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.00007185748,0.00003227341,0.04161013,0.0002262637,0.00003127626,5.604831e-7,0.0005192023,0.02376056,0.9333931,0.0002508679,0.00003994504,0.00006393937],"study_design_scores_gemma":[0.001185366,0.00001977861,0.006036469,0.000103697,0.00001989883,0.000008344563,0.0003034027,0.003871672,0.9880319,0.0002179162,0.00002958599,0.0001719667],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9770399,0.000008780581,0.02221088,0.0002550861,0.00007669417,0.0002143792,0.00001083644,0.00004221798,0.0001411779],"genre_scores_gemma":[0.9973046,0.000001478318,0.001890075,0.00008375043,0.00007047089,0.00002494343,0.0002751706,0.0000460686,0.0003034757],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.05463877,"threshold_uncertainty_score":0.9997432,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01477383417110699,"score_gpt":0.2693646611263477,"score_spread":0.2545908269552407,"validation_status":"score_only:v0-immature-baseline","note":"Baseline scores from an immature model (maturity gate not passed). Scores rank; they never assert a category."}}