{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,10]],"date-time":"2026-03-10T14:01:22Z","timestamp":1773151282901,"version":"3.50.1"},"reference-count":107,"publisher":"Wiley","issue":"55","license":[{"start":{"date-parts":[[2021,8,16]],"date-time":"2021-08-16T00:00:00Z","timestamp":1629072000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100005049","name":"Science and Engineering Research Council","doi-asserted-by":"publisher","award":["EMR\/2016\/007021"],"award-info":[{"award-number":["EMR\/2016\/007021"]}],"id":[{"id":"10.13039\/501100005049","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The direct C2\u2010functionalization of pyridines through a transition\u2010metal\u2010free protocol by using aryne multicomponent coupling is demonstrated. The reaction allowed a broad\u2010scope synthesis of C2\u2010substituted pyridine derivatives bearing the \u2212CF<jats:sub>3<\/jats:sub> group in good yields with \u03b1,\u03b1,\u03b1\u2010trifluoroacetophenones as the third component. Activated keto esters could also be employed as the third component in this formal 1,2\u2010di(hetero)arylation of ketones. Performing the reaction under dilute conditions inhibited the competing pyridine\u2013aryne polymerization pathway. Nucleophilic attack by the initially generated pyridylidene intermediate on the carbonyl followed by an S<jats:sub>N<\/jats:sub>Ar process resembling the Smiles rearrangement affords the desired products.<\/jats:p>","DOI":"10.1002\/chem.202102005","type":"journal-article","created":{"date-parts":[[2021,7,21]],"date-time":"2021-07-21T05:21:56Z","timestamp":1626844916000},"page":"13864-13869","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Transition\u2010Metal\u2010Free C2\u2010Functionalization of Pyridines through Aryne Three\u2010Component Coupling"],"prefix":"10.1002","volume":"27","author":[{"given":"Avishek","family":"Guin","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry Indian Institute of Science  Bangalore 560012 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Subrata","family":"Bhattacharjee","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Indian Institute of Science  Bangalore 560012 India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Akkattu T.","family":"Biju","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry Indian Institute of Science  Bangalore 560012 India"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,8,16]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For reviews see:"},{"key":"e_1_2_7_2_2","first-page":"1","volume":"1","author":"Altaf A. 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Lett."},{"key":"e_1_2_7_84_1","doi-asserted-by":"publisher","DOI":"10.1021\/ma048668b"},{"key":"e_1_2_7_85_1","volume":"1454","author":"Pe\u00f1a D.","year":"2002","journal-title":"Synthesis"},{"key":"e_1_2_7_86_1","unstructured":"See the Supporting Information for details."},{"key":"e_1_2_7_87_1","unstructured":"When2\u2009awas added to the stirring mixture of1\u2009aand3\u2009aunder the optimized conditions after 6\u2005h product4\u2009awas formed in 85\u2009% yield thus indicating that no appreciable polymerization happens under these conditions."},{"key":"e_1_2_7_88_1","unstructured":"For reports on rgioselective addition to 3-methoxy benzyne see:"},{"key":"e_1_2_7_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201609111"},{"key":"e_1_2_7_89_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201609111"},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja5099935"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00133a031"},{"key":"e_1_2_7_92_1","unstructured":"Deposition Number2058073 (4\u2009an)contains the supplementary crystallographic data for this paper. 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