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Homolytic aromatic substitution of acyl radicals: Oxidative coupling of 2-methylquinolines with quinoxalines

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Oxidative coupling of 2-methylquinolines with quinoxalines via a TBHP (t-butyl hydroperoxide) and TFA (trifluoroacetic acid) mediated Minisci reaction affords quinolin-2-yl(quinoxalin-2-yl)methanone derivatives. This approach provides a simple and efficient method to… Click to show full abstract

Oxidative coupling of 2-methylquinolines with quinoxalines via a TBHP (t-butyl hydroperoxide) and TFA (trifluoroacetic acid) mediated Minisci reaction affords quinolin-2-yl(quinoxalin-2-yl)methanone derivatives. This approach provides a simple and efficient method to construct various acyl derivatives in moderate to good yields (45%–92%) without any metal catalyst. Mechanistically, homolytic aromatic substitution (HAS) of acyl radicals mediated by TBHP is crucial for the construction of the quinolin-2-yl(quinoxalin-2-yl)methanone products.

Keywords: aromatic substitution; substitution acyl; methylquinolines quinoxalines; coupling methylquinolines; oxidative coupling; homolytic aromatic

Journal Title: Journal of Chemical Research
Year Published: 2022

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