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Transition Metal‐Free Regioselective Remote C−H Bond 2,2,2‐Trifluoroethoxylation of 8‐Aminoquinoline Derivatives at the C5 Position
Author(s) -
Ruyet Louise,
Poisson Thomas,
Besset Tatiana
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100580
Subject(s) - regioselectivity , chemistry , transition metal , yield (engineering) , combinatorial chemistry , quinoline , stereochemistry , organic chemistry , catalysis , metallurgy , materials science
The regioselective 2,2,2‐trifluoroethoxylation at the C5 position of amides derived from the 8‐aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal‐free transformation was achieved using the readily available and appealing 2,2,2‐trifluoroethanol as the fluorinated source. The selective distal 2,2,2‐trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61 % yield). This approach provided efficient access to high‐value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.