Journal
ISCIENCE
Volume 23, Issue 11, Pages -Publisher
CELL PRESS
DOI: 10.1016/j.isci.2020.101705
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Funding
- Henan University
- National Natural Science Foundation of China [21801061]
- Natural Science Foundation of Shandong Province [ZR2019MEM026, ZR2019BB026]
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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 CF3-containing iminoisoindolinones and polyamides by utilizing challenging CF3-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.
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