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An Efficient Waste-Free Oxidative Coupling via Regioselective C−H Bond Cleavage:  Rh/Cu-Catalyzed Reaction of Benzoic Acids with Alkynes and Acrylates under Air

Organic Letters · 2007 · Vol. 9(7) · pp. 1407–1409
Kenji UeuraTetsuya SatohMasahiro Miura

Abstract

[structure: see text]. The direct oxidative coupling of benzoic acids with internal alkynes proceeds efficiently in the presence of a rhodium/copper catalyst system under air to afford the corresponding isocoumarin derivatives. The reaction forms no wastes except for water. Under similar conditions, the aerobic coupling with acrylates also takes place smoothly to produce 7-vinylphthalide derivatives via divinylation and subsequent cyclization.

Catalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical ReactionsChemistryRegioselectivityCatalysisBond cleavageOxidative phosphorylationOxidative coupling of methaneBenzoic acidOxidative cleavageCleavage (geology)Medicinal chemistry
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An Efficient Waste-Free Oxidative Coupling via Regioselective C−H Bond Cleavage:  Rh/Cu-Catalyzed Reaction of Benzoic Acids with Alkynes and Acrylates under Air · Scinovex