{"id":"W4413659568","doi":"10.26434/chemrxiv-2025-hk0d9","title":"The Atroposelective Iodination of 2-Amino-6-arylpyridines Catalyzed by Chiral Disulfonimides Actually Proceeds via Brønsted Base Catalysis: A Combined Experimental and Computational Study","year":2025,"lang":"en","type":"preprint","venue":"ChemRxiv","topic":"Axial and Atropisomeric Chirality Synthesis","field":"Chemistry","cited_by":0,"is_retracted":false,"has_abstract":true,"ca_institutions":"","funders":"Division of Chemistry; Natural Sciences and Engineering Research Council of Canada; University of Illinois at Urbana-Champaign; W. M. Keck Foundation; National Science Foundation","keywords":"Catalysis; Halogenation; Base (topology); Chemistry; Brønsted–Lowry acid–base theory; Combinatorial chemistry; Medicinal chemistry; Organic chemistry; Mathematics","routes":{"ca_aff":false,"ca_fund":true,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":true},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0004838615,0.0007791875,0.0008129981,0.0003528748,0.0003697974,0.0006892449,0.0009300378,0.0005456021,0.00325077],"category_scores_gemma":[0.0005236946,0.0002407064,0.0005628574,0.0003878314,0.0003171424,0.0006583099,0.0002982384,0.0006478019,0.000474491],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0006910276,"about_ca_system_score_gemma":0.0008767958,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.004044342,"about_ca_topic_score_gemma":0.006182492,"domain_scores_codex":[0.9998771,0.00001927683,0.00000589381,0.00002070982,0.00004211661,0.00003497451],"domain_scores_gemma":[0.9998185,0.0001041902,0.00002363836,0.00001549291,0.00002752489,0.00001073184],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"simulation_or_modeling","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.0007471755,0.0004217123,0.006047068,0.002730313,0.0002068482,0.001142861,0.0001421462,0.8694838,0.04603871,0.04215666,0.002382451,0.02850027],"study_design_scores_gemma":[0.0001676587,0.0006736014,0.0009563348,0.00006632363,0.0001091101,0.0001160143,0.0001182701,0.9394057,0.04922689,0.004544689,0.004576961,0.00003852593],"study_design_candidate":"bench_or_experimental","study_design_consensus":null,"genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9535632,0.001646132,0.01569926,0.0002668652,0.0000479407,0.0000589714,0.001804359,0.0003625095,0.02655078],"genre_scores_gemma":[0.9863546,0.001203401,0.009967067,0.00004440348,0.000009040215,0.00004596503,0.001177683,0.00005054924,0.001147228],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.004044342,"threshold_uncertainty_score":0.01087493,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01038300510480549,"score_gpt":0.251246774947447,"score_spread":0.2408637698426415,"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."}}