{"id":"W2921319013","doi":"10.1002/anie.201900095","title":"PAd2‐DalPhos Enables the Nickel‐Catalyzed C−N Cross‐Coupling of Primary Heteroarylamines and (Hetero)aryl Chlorides","year":2019,"lang":"en","type":"article","venue":"Angewandte Chemie International Edition","topic":"Catalytic Cross-Coupling Reactions","field":"Chemistry","cited_by":79,"is_retracted":false,"has_abstract":true,"ca_institutions":"University of Alberta; Dalhousie University","funders":"Natural Sciences and Engineering Research Council of Canada; Dalhousie University","keywords":"Aryl; Catalysis; Pharmacophore; Nickel; Heteroatom; Primary (astronomy); Combinatorial chemistry; Chemistry; Ring (chemistry); Molecule; Metal; Base (topology); Coupling (piping); Stereochemistry; Materials science; Organic chemistry; Physics; Mathematics; Metallurgy","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":[],"consensus_categories":[],"category_scores_codex":[0.000202931,0.0002284673,0.0002557209,0.00008148218,0.000126264,0.0001581369,0.0003581921,0.0001485087,0.0006586075],"category_scores_gemma":[0.0001778072,0.0001928235,0.000152792,0.00009896254,0.0002763516,0.0005124055,0.0001853708,0.0002448078,0.00004013293],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0001766539,"about_ca_system_score_gemma":0.00005415918,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0001864479,"about_ca_topic_score_gemma":0.00001366673,"domain_scores_codex":[0.9984387,2.499928e-7,0.0004576522,0.0004063627,0.0004713754,0.0002256166],"domain_scores_gemma":[0.9985715,0.0003728289,0.0003197509,0.0004034605,0.0002729118,0.00005958547],"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":[0.000108271,0.00008180744,0.01262745,0.0001754572,0.0001280299,0.000002918694,0.0001840122,0.0001234199,0.9854328,0.00006722273,0.0008628896,0.0002057275],"study_design_scores_gemma":[0.0008532688,0.00001111287,0.005711605,0.0001672519,0.00004182888,0.00005473901,0.0001727744,0.0008215344,0.9898633,0.0003231134,0.001779308,0.0002001326],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9964572,0.0002824756,0.00005165354,0.0004796268,0.001039397,0.0001217517,0.0002482308,0.00008163934,0.001238014],"genre_scores_gemma":[0.9952303,0.0001955501,0.00001708732,0.00009033176,0.00108293,0.00005149917,0.001291921,0.00003570037,0.002004747],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.006915845,"threshold_uncertainty_score":0.7863112,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01244534459657107,"score_gpt":0.2550779192613182,"score_spread":0.2426325746647471,"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."}}