Journal
GREEN CHEMISTRY
Volume 25, Issue 8, Pages 3034-3039Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3gc00267e
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A metal-free and efficient method for the synthesis of 1,2-diketones through oxidative C(sp)-H functionalization of alkynes has been developed. The oxidative addition of a phenyl radical generated from aniline to terminal alkynes, aided by a composite of tert-butyl nitrite and ascorbic acid, leads to the formation of α-diketones. This one-pot strategy employs 2-methyltetrahydrofuran (2-MeTHF) as an alternative reaction medium for the oxidative diketonation. The method allows for the synthesis of symmetrical and unsymmetrical substituted 1,2-diketones using easily accessible reactants, and offers promising features such as environmentally benign reagents, greener and renewable solvents, a broad range of substrates, large-scale synthesis, lower E-factors, practical applications, radical pathways, and mild reaction conditions.
A metal-free and efficient oxidative C(sp)-H functionalization of alkynes has been developed for the synthesis of 1,2-diketones. A composite of tert-butyl nitrite and ascorbic acid effectively promoted the oxidative addition of a phenyl radical generated from aniline to terminal alkynes producing a-diketones. The one-pot strategy involves 2-methyltetrahydrofuran (2-MeTHF) as a useful alternative reaction medium for oxidative diketonation. Furthermore, the protocol provides a novel route to symmetrical and unsymmetrical substituted 1,2-diketones from easily accessible reactants. Notably, environmentally benign reagents, greener and renewable solvents, a broad range of substrates, large-scale synthesis, lower E-factors, practical applications, radical pathways and mild conditions are the promising features of the present method.
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