Catalyst-free aroylation of maleimides through Csp2–H functionalization with aldehydes and benzyl phenyl sulfides†
a
and
Farnaz
Jafarpour
*a
Abstract
Aroyl maleimides and their derivatives have potential applications as inhibitors, fluorophores, antibiotics, and anticonvulsants. The Friedel–Crafts method, as the renowned aroylation method of arenes and heteroarenes, is tedious and suffers from harsh conditions, incompatibility with electron-deficient substrates, and Lewis acid deactivation due to its coordination with the nitrogen of substrates. Hence, two eco-friendly and feasible metal-free di-tert-butyl peroxide-promoted methods are developed for the aroylation of maleimides toward 3,4-diaroyl maleimides and 3-amino-4-aroyl maleimides. These include the direct cross-dehydrogenative coupling of maleimides with aryl aldehydes and the tandem oxidative C–S cleavage/cross-dehydrogenative coupling of benzyl phenyl sulfides with maleimides. The results indicate the efficiency of the presented approaches with broad scopes.
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