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Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper\u2010catalyzed synthesis of ynimines from readily available <jats:italic>O\u2010<\/jats:italic>acetyl ketoximes and terminal alkynes. A wide range of <jats:italic>O<\/jats:italic>\u2010acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross\u2010coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.<\/jats:p>","DOI":"10.1002\/anie.202110901","type":"journal-article","created":{"date-parts":[[2021,9,1]],"date-time":"2021-09-01T15:43:52Z","timestamp":1630511032000},"page":"24028-24033","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":34,"title":["Copper\u2010Catalyzed Aza\u2010Sonogashira Cross\u2010Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles"],"prefix":"10.1002","volume":"60","author":[{"given":"R\u00e9mi","family":"Lavernhe","sequence":"first","affiliation":[{"name":"Laboratory of Synthesis and Natural Products Institute of Chemical Sciences and Engineering Ecole Polytechnique Federal de Lausanne  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