Reported here is ac opper-catalyzed 1,2-methoxy methoxycarbonylation of alkenes by an unprecedented use of methyl formate as as ource of both the methoxy and the methoxycarbonyl groups.This reaction transforms styrene and its derivatives into value-added b-methoxy alkanoates and cinnamates,a sw ell as medicinally important five-membered heterocycles,s uch as functionalized tetrahydrofurans, g-lactones,a nd pyrrolidines.Aternary b-diketiminato-Cu I -styrene complex, fully characterized by NMR spectroscopyand X-ray crystallographic analysis,i sc apable of catalyzing the same transformation. These findings suggest that pre-coordination of electron-richalkenes to copper might play an important role in accelerating the addition of nucleophilic radicals to electronrich alkenes,and could have general implications in the design of novel radical-based transformations.
Reported here is ac opper-catalyzed 1,2-methoxy methoxycarbonylation of alkenes by an unprecedented use of methyl formate as as ource of both the methoxy and the methoxycarbonyl groups.This reaction transforms styrene and its derivatives into value-added b-methoxy alkanoates and cinnamates,a sw ell as medicinally important five-membered heterocycles,s uch as functionalized tetrahydrofurans, g-lactones,a nd pyrrolidines.Aternary b-diketiminato-Cu I -styrene complex, fully characterized by NMR spectroscopyand X-ray crystallographic analysis,i sc apable of catalyzing the same transformation. These findings suggest that pre-coordination of electron-richalkenes to copper might play an important role in accelerating the addition of nucleophilic radicals to electronrich alkenes,and could have general implications in the design of novel radical-based transformations.
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