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A Mild and efficient synthesis of substituted quinolines via a cross-dehydrogenative coupling of (bio)available alcohols and aminoarenes

Mura, Manuel Giacomo and Rajamäki, Suvi and De Luca, Lidia Vera Giovanna and Cini, Elena and Porcheddu, Andrea (2015) A Mild and efficient synthesis of substituted quinolines via a cross-dehydrogenative coupling of (bio)available alcohols and aminoarenes. Advanced Synthesis & Catalysis, Vol. 357 (2-3), p. 576-582. ISSN 1615-4150. Article.

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DOI: 10.1002/adsc.201400815

Abstract

A ruthenium-catalysed dehydrogenative cross-coupling of primary alcohols and imines in the presence of TFA provided a library of differently substituted quinolines. Imines can be prepared in situ from various anilines and several benzyl alcohols using a ruthenium-catalysed hydrogen-transfer procedure. Without changing the catalyst, quinolines can be obtained in moderate to good yields by adding various primary alcohols in the presence of TFA (30 mol%) via a “telescopic” protocol. The use of alcohols, the absence of strong oxidants and the diversity of potential starting materials make this modern version of the Skraup reaction superior to most of the conventional quinoline syntheses.

Item Type:Article
ID Code:10925
Status:Published
Refereed:Yes
Uncontrolled Keywords:Alcohols, cross-coupling reactions, microwave irradiation, quinolines, transfer hydrogenation
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:Wiley
ISSN:1615-4150
Deposited On:10 Jun 2015 16:24

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