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N-Acyl amidines in particular can be used as a starting material for the synthesis of heterocycles and have several other applications. Here, we describe a fast and practical copper-catalyzed three-component reaction of aryl acetylenes, amines, and easily accessible 1,4,2-dioxazol-5-ones to N-acyl amidines, generating CO2 as the only byproduct. Transformation of the dioxazolones on the Cu catalyst generates acyl nitrenes that rapidly insert into the copper acetylide Cu\u2013C bond rather than undergoing an undesired Curtius rearrangement. For nonaromatic dioxazolones, [Cu(OAc)(Xantphos)] is a superior catalyst for this transformation, leading to full substrate conversion within 10 min. For the direct synthesis of N-benzoyl amidine derivatives from aromatic dioxazolones, [Cu(OAc)(Xantphos)] proved to be inactive, but moderate to good yields were obtained when using simple copper(I) iodide (CuI) as the catalyst. Mechanistic studies revealed the aerobic instability of one of the intermediates at low catalyst loadings, but the reaction could still be performed in air for most substrates when using catalyst loadings of 5 mol %. The herein reported procedure not only provides a new, practical, and direct route to N-acyl amidines but also represents a new type of C\u2013N bond formation.<\/jats:p>","DOI":"10.1021\/jacs.9b07140","type":"journal-article","created":{"date-parts":[[2019,8,29]],"date-time":"2019-08-29T15:13:55Z","timestamp":1567091635000},"page":"15240-15249","source":"Crossref","is-referenced-by-count":93,"title":["Efficient Copper-Catalyzed Multicomponent Synthesis\nof\n                    <i>N-<\/i>\n                    Acyl Amidines via Acyl Nitrenes"],"prefix":"10.1021","volume":"141","author":[{"given":"Kaj M.","family":"van Vliet","sequence":"first","affiliation":[{"name":"Universiteit van Amsterdam (UvA) , , ,","place":["Amsterdam, The Netherlands, 1012 WX"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6013-6215","authenticated-orcid":true,"given":"Lara H.","family":"Polak","sequence":"additional","affiliation":[{"name":"Universiteit van Amsterdam (UvA) , , ,","place":["Amsterdam, The Netherlands, 1012 WX"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4165-7810","authenticated-orcid":true,"given":"Maxime A.","family":"Siegler","sequence":"additional","affiliation":[{"name":"John Hopkins University , , , ,","place":["Baltimore, Maryland, United States, 21218"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0665-9239","authenticated-orcid":true,"given":"Jarl Ivar","family":"van der Vlugt","sequence":"additional","affiliation":[{"name":"Universiteit van Amsterdam (UvA) , , ,","place":["Amsterdam, The Netherlands, 1012 WX"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2973-5321","authenticated-orcid":true,"given":"Ce\u0301lia Fonseca","family":"Guerra","sequence":"additional","affiliation":[{"name":"Vrije Universiteit Amsterdam (VU) , , De Boelelaan 1083 , ,","place":["Amsterdam, The Netherlands, 1081 HV"]},{"name":"U\u0301niversiteit Leiden , , Einsteinweg 55 , ,","place":["Leiden, The Netherlands, 2333 CC"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3482-7669","authenticated-orcid":true,"given":"Bas","family":"de Bruin","sequence":"additional","affiliation":[{"name":"Universiteit van Amsterdam (UvA) , , ,","place":["Amsterdam, The Netherlands, 1012 WX"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,8,29]]},"reference":[{"key":"2026090313464940400_cit1","doi-asserted-by":"publisher","first-page":"790","DOI":"10.2174\/1385272819666150402221133","article-title":"1,8-Diazabicyclo[5.4.0]Undec-7-Ene\n(DBU): A Versatile Reagent in Organic Synthesis","volume":"19","author":"Nand","year":"2015","journal-title":"Curr. 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Catal."},{"key":"2026090313464940400_cit29","doi-asserted-by":"publisher","first-page":"9769","DOI":"10.1021\/jo7016247","article-title":"Phosphoryl\nAzides as Versatile New\nReaction Partners in the Cu-Catalyzed Three-Component Couplings","volume":"72","author":"Seok","year":"2007","journal-title":"J. Org. Chem."},{"key":"2026090313464940400_cit30","doi-asserted-by":"publisher","first-page":"2038","DOI":"10.1021\/ja0432968","article-title":"Highly Efficient One-Pot Synthesis of N-Sulfonylamidines\nby Cu-Catalyzed Three-Component Coupling of Sulfonyl Azide, Alkyne,\nand Amine","volume":"127","author":"Bae","year":"2005","journal-title":"J. Am. Chem. 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