A photoredox-mediated acylation reaction of electron deficient heteroarenes with terminal alkynes is reported. The method relies on oxidative cleavage of phenylacetylenes for generation of acyl radicals as a key enabling feature. The reaction is regioselective with broad substrate scope. Quantum yield investigations support a radical chain mechanism.
A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene−alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.
Synthesis of ketones is one of the most addressed problems in organic chemistry owing to their presence in a diverse array of drugs, pharmaceuticals, natural products and photosensitizers. Many of the limitations associated with the traditional approaches enabling the synthesis of ketones like creation of high energy acylating reagents, poor functional group tolerance, pre-activation of starting materials have been largely addressed with the advent of photoredox chemistry. This review summarizes the recent advances made in the photoredox catalyzed synthesis of ketones. 2 3 4 5 6 7 8
As imple and practical method for synthesizing a-ketoamidesh as been developed involving Cu(OTf) 2 -promoted oxidative amidation-diketonization of terminal alkynes with primary/secondary amines. This method has aw ide substrate scope, and atmospheric oxygen acts as the oxidant.
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