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Herein, we report a rhodium\u2010catalyzed pyridylation of alkynamides with pyridylboronic acids, producing a variety of primary, secondary, and tertiary enamides with high yields (up to 94\u2009%). This reaction demonstrates broad tolerance towards various alkyl and aryl functional groups, providing convenient access to a diverse array of alkenylpyridine derivatives. To demonstrate potential applications in late\u2010stage hydropyridylation, we synthesized \u03b1,\u03b2\u2010unsaturated ketones, aldehydes, and esters with high yields from the pyridylation product of Weinreb amides. This indirect expansion of the substrate scope enhances the practicality of this strategy. Additionally, the \u03b1,\u03b2\u2010unsaturated ketone obtained can be further reduced to yield a chiral alcohol with a 99\u2009% <jats:italic>ee<\/jats:italic>, further demonstrating the versatility and potential utility of this approach.<\/jats:p>","DOI":"10.1002\/chem.202401830","type":"journal-article","created":{"date-parts":[[2024,7,22]],"date-time":"2024-07-22T10:59:15Z","timestamp":1721645955000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Rhodium\u2010Catalyzed Pyridylation of Alkynamides with Pyridylboronic Acids: A Route to Functionalized Enamides"],"prefix":"10.1002","volume":"30","author":[{"given":"Huilong","family":"Zhu","sequence":"first","affiliation":[{"name":"Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy School of Pharmacy Xuzhou Medical University  Xuzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dingcheng","family":"Sun","sequence":"additional","affiliation":[{"name":"Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy School of Pharmacy Xuzhou Medical University  Xuzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shengxiang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy School of Pharmacy Xuzhou Medical University  Xuzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Junning","family":"Chen","sequence":"additional","affiliation":[{"name":"Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy School of Pharmacy Xuzhou Medical University  Xuzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9703-8245","authenticated-orcid":false,"given":"Zhou","family":"Xu","sequence":"additional","affiliation":[{"name":"Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy School of Pharmacy Xuzhou Medical University  Xuzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,9,9]]},"reference":[{"key":"e_1_2_8_1_1","first-page":"537","volume":"21","author":"Lipton M. 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