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A Mild and Efficient Synthesis of Substituted Quinolines via a Cross‐Dehydrogenative Coupling of (Bio)available Alcohols and Aminoarenes
Author(s) -
Mura Manuel G.,
Rajamäki Suvi,
De Luca Lidia,
Cini Elena,
Porcheddu Andrea
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400815
Subject(s) - chemistry , ruthenium , quinoline , catalysis , primary (astronomy) , transfer hydrogenation , combinatorial chemistry , organic chemistry , physics , astronomy
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.