Transition Metal‐Free Regioselective Remote C−H Bond 2,2,2‐Trifluoroethoxylation of 8‐Aminoquinoline Derivatives at the C5 Position - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

Transition Metal‐Free Regioselective Remote C−H Bond 2,2,2‐Trifluoroethoxylation of 8‐Aminoquinoline Derivatives at the C5 Position

Résumé

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.

Domaines

Chimie organique
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Dates et versions

hal-03443130 , version 1 (23-11-2021)

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Citer

Louise Ruyet, Thomas Poisson, Tatiana Besset. Transition Metal‐Free Regioselective Remote C−H Bond 2,2,2‐Trifluoroethoxylation of 8‐Aminoquinoline Derivatives at the C5 Position. European Journal of Organic Chemistry, 2021, 2021 (23), pp.3407-3410. ⟨10.1002/ejoc.202100580⟩. ⟨hal-03443130⟩
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