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This oxidative protocol can be applied to both sterically and electronically challenging substrates in a highly chemoselective, practical, and rapid manner. The use of cyclopropyl and thioether substrates support the radical formation of \u03b1\u2010peroxy malononitrile species, which can cyclize to dioxiranes that can monooxygenate malononitrile \u03b1\u2010carbanions to afford activated acyl cyanides capable of reacting with amine nucleophiles.<\/jats:p>","DOI":"10.1002\/anie.201603399","type":"journal-article","created":{"date-parts":[[2016,6,14]],"date-time":"2016-06-14T16:08:49Z","timestamp":1465920529000},"page":"9060-9064","source":"Crossref","is-referenced-by-count":62,"title":["Sterically Demanding Oxidative Amidation of \u03b1\u2010Substituted Malononitriles with Amines Using O<sub>2<\/sub>"],"prefix":"10.1002","volume":"55","author":[{"given":"Jing","family":"Li","sequence":"first","affiliation":[{"name":"Department of Chemistry, Graduate School of Science Tohoku University  Aza Aramaki Aoba-ku Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2556-2029","authenticated-orcid":false,"given":"Martin J.","family":"Lear","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Lincoln  Brayford Pool Lincoln LN6 7TS UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yujiro","family":"Hayashi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Science Tohoku University  Aza Aramaki Aoba-ku Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,6,14]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/352760068X"},{"key":"e_1_2_2_3_2","volume-title":"Chemistry, Biochemistry and Materials Science","year":"2003"},{"key":"e_1_2_2_4_2","volume-title":"Peptide Drug Discovery and Development","year":"2011"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/B701677H"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100048w"},{"key":"e_1_2_2_8_1","unstructured":"Seminal methods to making challenging amide bonds:"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature10702"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204481"},{"key":"e_1_2_2_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204481"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja409012q"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja510135t"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906005j"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja806063k"},{"key":"e_1_2_2_15_1","unstructured":"Leading oxidative methods to making amide bonds using alternative starting materials:"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1145295"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0764052"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature09125"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107198"},{"key":"e_1_2_2_19_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201107198"},{"key":"e_1_2_2_19_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201308614"},{"key":"e_1_2_2_19_5","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201308614"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201511486"},{"key":"e_1_2_2_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201511486"},{"key":"e_1_2_2_21_1","unstructured":"Discovery development and mechanistic studies of the base-promoted Nef reaction and oxidative amidation of nitroalkanes by O2:"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201209380"},{"key":"e_1_2_2_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201209380"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403475"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505192"},{"key":"e_1_2_2_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201505192"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201600540"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00302a008"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.11.016"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1213920"},{"key":"e_1_2_2_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.08.038"},{"key":"e_1_2_2_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo030046l"},{"key":"e_1_2_2_31_1","unstructured":"Related reports on ketone formation from alkylnitriles using O2:"},{"key":"e_1_2_2_32_2","first-page":"1983","author":"Kulp S. 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