Construction of 4‐Isochromanones through Cu(OTf)<sub>2</sub>‐Catalysed Sequential C=O and C–O Bond Formation

Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules.I nspired by the redox diversity of these features in nature,w ed emonstrate herein ar edox-divergent construction of dihydrothiophenes,thiophenes,and bromothiophenes from the respective readily available allylic alcohols,d imethyl sulfoxide (DMSO), and HBr.T he redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr.M echanistic studies suggest that DMSO simultaneously acts as an oxidant and as ulfur donor.T he synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations,i ncluding the preparation of bioactive and functional molecules.

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Redox‐Divergent Construction of (Dihydro)thiophenes with DMSO

Liu

¹

,

He

²

,

Zhao

³

et al. 2021

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Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules.I nspired by the redox diversity of these features in nature,w ed emonstrate herein ar edox-divergent construction of dihydrothiophenes,thiophenes,and bromothiophenes from the respective readily available allylic alcohols,d imethyl sulfoxide (DMSO), and HBr.T he redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr.M echanistic studies suggest that DMSO simultaneously acts as an oxidant and as ulfur donor.T he synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations,i ncluding the preparation of bioactive and functional molecules.

show abstract