{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T20:06:47Z","timestamp":1790712407525,"version":"4.1.0"},"reference-count":57,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2018,8,27]],"date-time":"2018-08-27T00:00:00Z","timestamp":1535328000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000009","name":"Foundation for the National Institutes of Health","doi-asserted-by":"publisher","award":["R01 GM124094"],"award-info":[{"award-number":["R01 GM124094"]}],"id":[{"id":"10.13039\/100000009","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,9,17]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Coupling aromatic heteronucleophiles to arenes is a common way to assemble drug\u2010like molecules. Many methods operate via nucleophiles intercepting organometallic intermediates, via Pd\u2010, Cu\u2010, and Ni\u2010catalysis, that facilitate carbon\u2010heteroatom bond formation and a variety of protocols. We present an alternative, unified strategy where phosphonium salts can replicate the behavior of organometallic intermediates. Under a narrow set of reaction conditions, a variety of aromatic heteronucleophile classes can be coupled to pyridines and diazines that are often problematic in metal\u2010catalyzed couplings, such as where (pseudo)halide precursors are unavailable in complex structures with multiple polar functional groups.<\/jats:p>","DOI":"10.1002\/anie.201807322","type":"journal-article","created":{"date-parts":[[2018,8,7]],"date-time":"2018-08-07T11:46:40Z","timestamp":1533642400000},"page":"12514-12518","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":89,"title":["A Unified Approach to Couple Aromatic Heteronucleophiles to Azines and Pharmaceuticals"],"prefix":"10.1002","volume":"57","author":[{"given":"Ryan G.","family":"Anderson","sequence":"first","affiliation":[{"name":"Department of Chemistry Colorado State University  Fort Collins Colorado 80523 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brianna M.","family":"Jett","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  Fort Collins Colorado 80523 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8651-1631","authenticated-orcid":false,"given":"Andrew","family":"McNally","sequence":"additional","affiliation":[{"name":"Department of Chemistry Colorado State University  Fort Collins Colorado 80523 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,8,27]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tips.2015.04.005"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1017\/S0033583508004745"},{"key":"e_1_2_2_3_1","unstructured":"For examples of SNAr reactions see:"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/c4ra04851b"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja070021u"},{"key":"e_1_2_2_6_1","unstructured":"For reviews see:"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800497"},{"key":"e_1_2_2_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800497"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00512"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar800098p"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700391"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100259t"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300594"},{"key":"e_1_2_2_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200300594"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201701690"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201701690"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201301500"},{"key":"e_1_2_2_15_1","unstructured":"For examples of recent light-driven processes see:"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aag0209"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1226458"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b03744"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja4060806"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja404050f"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC00368C"},{"key":"e_1_2_2_22_1","volume-title":"Ligand Coupling Reactions with Heteroaromatic Compounds, Vol.\u200518","author":"Finet J. 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