{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T16:17:58Z","timestamp":1787242678347,"version":"build-2736575974"},"reference-count":73,"publisher":"Wiley","issue":"38","license":[{"start":{"date-parts":[[2022,7,19]],"date-time":"2022-07-19T00:00:00Z","timestamp":1658188800000},"content-version":"am","delay-in-days":337,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"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\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-1855556"],"award-info":[{"award-number":["CHE-1855556"]}],"id":[{"id":"10.13039\/100000165","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000165","name":"Division of Chemistry","doi-asserted-by":"publisher","award":["CHE-1654122"],"award-info":[{"award-number":["CHE-1654122"]}],"id":[{"id":"10.13039\/100000165","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":[[2021,9,13]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Ketone functionalization is a cornerstone of organic synthesis. Herein, we describe the development of an intermolecular C\u2212H alkenylation of enamides with the feedstock chemical vinyl acetate to access diverse functionalized ketones. Enamides derived from various cyclic and acyclic ketones reacted efficiently, and a number of sensitive functional groups were tolerated. In this iridium\u2010catalyzed transformation, two structurally and electronically similar alkenes\u2014enamide and vinyl acetate\u2014underwent selective cross\u2010coupling through C\u2212H activation. No reaction partner was used in large excess. The reaction is also pH\u2010 and redox\u2010neutral with HOAc as the only stoichiometric by\u2010product. Detailed experimental and computational studies revealed a reaction mechanism involving 1,2\u2010Ir\u2010C migratory insertion followed by\n                    <jats:italic>syn<\/jats:italic>\n                    \u2010\u03b2\u2010acetoxy elimination, which is different from that of previous vinyl acetate mediated C\u2212H activation reactions. Finally, the alkenylation product can serve as a versatile intermediate to deliver a variety of structurally modified ketones.\n                  <\/jats:p>","DOI":"10.1002\/anie.202107331","type":"journal-article","created":{"date-parts":[[2021,7,19]],"date-time":"2021-07-19T13:09:11Z","timestamp":1626700151000},"page":"20926-20934","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Development and Mechanistic Studies of the Iridium\u2010Catalyzed C\u2212H Alkenylation of Enamides with Vinyl Acetates: A Versatile Approach for Ketone Functionalization"],"prefix":"10.1002","volume":"60","author":[{"given":"Bo","family":"Zhou","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Chicago  Chicago IL 60637 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaotian","family":"Qi","sequence":"additional","affiliation":[{"name":"College of Chemistry and Molecular Sciences Wuhan University  Wuhan Hubei 430072 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Pittsburgh  Pittsburgh PA 15260 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1331-6015","authenticated-orcid":false,"given":"Guangbin","family":"Dong","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Chicago  Chicago IL 60637 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,8,16]]},"reference":[{"key":"e_1_2_6_1_1","volume-title":"March's Advanced Organic Chemistry","author":"Smith M. 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This transition state has an activation free energy of 17.6\u2005kcal\u2009mol\u22121and is thus much less favorable than17\u2009b-TS. 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