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Article Dans Une Revue ACS Catalysis Année : 2022

Rapid and Mild Metal-Free Reduction of Epoxides to Primary Alcohols Mediated by HFIP

Résumé

The reduction of epoxides is a powerful tool to access anti-Markovnikov alcohols, but reported methods are poorly compatible with strongly electronically deactivated substrates. Here, we describe a general method for the linear-selective reduction of styryl oxides incorporating strong electron-withdrawing groups. The method remains compatible with more traditional epoxide motifs, such as aliphatic and electron-rich styrene oxides. Other (hetero)cycles such as oxetanes, tetrahydrofurans, aziridines, and cyclopropanes can also be reductively opened. This user-friendly reaction relies on the combination of a Brønsted acid catalyst and hexafluoroisopropanol as a solvent, and thus, in contrast to existing epoxide reduction methods, it does not require anhydrous reagents or an inert atmosphere. The generated primary alcohols can be conveniently functionalized in situ by a dehydrative Friedel–Crafts arylation without preactivation
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Dates et versions

hal-03622355 , version 1 (28-03-2022)

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Marie Vayer, Shaofei Zhang, Joseph Moran, David Lebœuf. Rapid and Mild Metal-Free Reduction of Epoxides to Primary Alcohols Mediated by HFIP. ACS Catalysis, 2022, 12 (6), pp.3309-3316. ⟨10.1021/acscatal.2c00216⟩. ⟨hal-03622355⟩
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