{"id":"W2330636615","doi":"10.1021/om500520z","title":"Palladium-Catalyzed Suzuki–Miyaura Cross-Couplings with 2-Diethylphosphonato-Substituted Aryl- and Naphthylboronate Esters as the Nucleophilic Partner: A Complementary Approach to the Synthesis of Biaryl Monophosphonates","year":2014,"lang":"en","type":"article","venue":"Organometallics","topic":"Catalytic Cross-Coupling Reactions","field":"Chemistry","cited_by":13,"is_retracted":false,"has_abstract":true,"ca_institutions":"Mount Allison University","funders":"Engineering and Physical Sciences Research Council; Newcastle University","keywords":"Chemistry; Phosphonate; Nucleophile; Aryl; Yield (engineering); Steric effects; Palladium; Electrophile; Combinatorial chemistry; Catalysis; Organic chemistry; Phosphine; Nucleophilic aromatic substitution; Coupling reaction; Medicinal chemistry; Stereochemistry; Nucleophilic substitution; Alkyl","routes":{"ca_aff":true,"ca_fund":false,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":false},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0003439206,0.0008166404,0.0004351315,0.0004183414,0.0002730823,0.0003492011,0.000488974,0.0005674877,0.001874591],"category_scores_gemma":[0.0002219071,0.0003411332,0.0003094453,0.0003190636,0.0002063951,0.0004502856,0.0006953063,0.0009260649,0.001580108],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.0003476199,"about_ca_system_score_gemma":0.0004669585,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0005191495,"about_ca_topic_score_gemma":0.001569559,"domain_scores_codex":[0.9997502,0.00004241249,0.0000281754,0.00005662271,0.00006260596,0.00006010264],"domain_scores_gemma":[0.9998777,0.00001952261,0.00002997144,0.00002097699,0.00001798102,0.00003383934],"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":[0.00004840823,0.0000185279,0.00005114737,0.0001299681,0.00001431615,0.0001574865,0.00005017584,0.0001378088,0.9953159,0.0003325325,0.0000440008,0.003699668],"study_design_scores_gemma":[0.000009465542,0.0001914757,0.000486338,0.00001131565,0.00002497089,0.0003375804,0.00001838641,0.0004610918,0.9942332,0.00009095152,0.004120386,0.00001483179],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9041058,0.01051715,0.06371138,0.0003080658,0.0001766423,0.0002680558,0.0006694084,0.0006110946,0.01963236],"genre_scores_gemma":[0.9528507,0.005826911,0.03285158,0.0001141714,0.00004095745,0.0001517467,0.0005676566,0.00009235493,0.007503915],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.001874591,"threshold_uncertainty_score":0.006271124,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01096422503656992,"score_gpt":0.2389342468766222,"score_spread":0.2279700218400523,"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."}}