{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T01:05:29Z","timestamp":1788915929768,"version":"build-2803163510"},"reference-count":36,"publisher":"Beilstein Institut","license":[{"start":{"date-parts":[[2020,3,26]],"date-time":"2020-03-26T00:00:00Z","timestamp":1585180800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2020,3,26]],"date-time":"2020-03-26T00:00:00Z","timestamp":1585180800000},"content-version":"am","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2020,3,26]],"date-time":"2020-03-26T00:00:00Z","timestamp":1585180800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Beilstein J. Org. Chem."],"accepted":{"date-parts":[[2020,3,13]]},"abstract":"<jats:p>A terminal alkyne is one of the most useful reactants for the synthesis of alkyne and alkene derivatives. Because an alkyne undergoes addition reaction at a C\u2013C triple bond or cross-coupling at a terminal C\u2013H bond. Combining those reaction patterns could realize a new reaction methodology to synthesize complex molecules including C\u2013C multiple bonds. In this report, we found that the reaction of 3 equivalents of terminal alkyne <jats:bold>1<\/jats:bold> (aryl substituted alkyne) and an \u03b1-bromocarbonyl compound <jats:bold>2<\/jats:bold> (tertiary alkyl radical precursor) undergoes tandem alkyl radical addition\/Sonogashira coupling to produce 1,3-enyne compound <jats:bold>3<\/jats:bold> possessing a quaternary carbon in the presence of a copper catalyst. Moreover, the reaction of \u03b1-bromocarbonyl compound <jats:bold>2<\/jats:bold> and an alkyne <jats:bold>4<\/jats:bold> possessing a carboxamide moiety undergoes tandem alkyl radical addition\/C\u2013H coupling to produce indolinone derivative <jats:bold>5<\/jats:bold>.<\/jats:p>","DOI":"10.3762\/bjoc.16.45","type":"journal-article","created":{"date-parts":[[2020,3,26]],"date-time":"2020-03-26T09:40:21Z","timestamp":1585215621000},"page":"502-508","source":"Crossref","is-referenced-by-count":7,"title":["Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary 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