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

Autor:	Marie Vayer, Shaofei Zhang, Joseph Moran, David Lebœuf
Přispěvatelé:	Institut de Science et d'ingénierie supramoléculaires (ISIS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS), univOAK, Archive ouverte
Rok vydání:	2022
Předmět:	Brønsted acid epoxides hexafluoroisopropanol [CHIM.ORGA]Chemical Sciences/Organic chemistry hydrogenolysis [CHIM.CATA] Chemical Sciences/Catalysis [CHIM.CATA]Chemical Sciences/Catalysis General Chemistry (hetero)cycles [CHIM.ORGA] Chemical Sciences/Organic chemistry Catalysis
Zdroj:	ACS Catalysis ACS Catalysis, 2022, 12 (6), pp.3309-3316. ⟨10.1021/acscatal.2c00216⟩
ISSN:	2155-5435
DOI:	10.1021/acscatal.2c00216
Popis:	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
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2c695299e5ba565f1af21189c5b683cf https://doi.org/10.1021/acscatal.2c00216 Zobrazit plný text záznamu