Three-Component Domino Acylation/Trifluoromethylation of Bicyclic Amidines.
Ziwei LuoJiahua ChenMengwan LiGavin Chit TsuiPublished in: Organic letters (2023)
We herein describe a three-component reaction involving bicyclic amidines such as DBN/DBU, acyl fluorides, and TMSCF 3 for access to a novel class of N -acyl trifluoromethylated bicyclic aminals. Under mild and operationally simple conditions, bicyclic amidines can undergo difunctionalization (acylation/trifluoromethylation) using readily available reagents. Further Lewis acid-promoted nucleophilic ring-opening can lead to diverse products with quaternary carbon centers containing CF 3 . The corresponding pentafluoroethylation is also achieved by using TMSC 2 F 5 .
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