Transition metal catalyzed [3 + 2] annulation of imines with double bonds via directed C-H activation offers a direct access to amino cyclic motifs. However, owing to weak coordination and steric hindrance, trifluoromethylated ketimines have been an unaddressed challenge for TM-catalyzed annulations. Here, a rhenium-catalyzed [3 + 2] annulation of trifluoromethylated ketimines with isocyanates via C(sp 2 )-H activation has been disclosed. This approach provides an efficient platform for rapid access to a privileged library of CF 3 -containing iminoisoindolinones and polyamides by utilizing challenging CF 3 -ketimines as the annulation component. The capability of gram scale synthesis, the post-functionalization of the cyclization adduct, the derivation of complex natural molecules and the facile synthesis of polyamides highlight a diversity of synthetic potential of the current methodology.
The coupling between heterocycle N-oxides and CF3-ynones has been demonstrated via the formal C−H and C−C bond cleavage under catalyst-free and mild conditions. This reaction has displayed broad substrate scope...
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