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Rapid and Mild Metal-Free Reduction of Epoxides to Primary Alcohols Mediated by HFIP
- Source :
- ACS Catalysis, ACS Catalysis, 2022, 12 (6), pp.3309-3316. ⟨10.1021/acscatal.2c00216⟩
- Publication Year :
- 2022
- Publisher :
- American Chemical Society (ACS), 2022.
-
Abstract
- 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
Details
- ISSN :
- 21555435
- Volume :
- 12
- Database :
- OpenAIRE
- Journal :
- ACS Catalysis
- Accession number :
- edsair.doi.dedup.....2c695299e5ba565f1af21189c5b683cf