Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons

• DOI: 10.3762/bjoc.16.45
• Publication Date: 2020-03-26T09:40:21Z
• Authors: Goki Hirata; Yu Yamane; Naoya Tsubaki; Reina Hara; Takashi Nishikata
• Keywords: Alkyne; Sonogashira coupling; Alkene; Coupling reaction; Triple bond; Moiety; Reactivity

A terminal alkyne is one of the most useful reactants for synthesis and alkene derivatives. Because an undergoes addition reaction at a C–C triple bond or cross-coupling C–H bond. Combining those patterns could realize new methodology to synthesize complex molecules including multiple bonds. In this report, we found that 3 equivalents 1 (aryl substituted alkyne) α-bromocarbonyl compound 2 (tertiary alkyl radical precursor) tandem addition/Sonogashira coupling produce 1,3-enyne possessing quaternary carbon in presence copper catalyst. Moreover, 4 carboxamide moiety addition/C–H indolinone derivative 5 .