The [3+2] Annulation of CF 3 -Ketimines by Re Catalysis: Access to CF 3 -Containing Amino Heterocycles and Polyamides

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...

Full description

Saved in:
Bibliographic Details
Published iniScience Vol. 23; no. 11; p. 101705
Main Authors Zhang, Saisai, Liu, Xun-Yong, Chang, Zhenbang, Qiao, Xinxin, Xiong, Heng-Ying, Zhang, Guangwu
Format Journal Article
LanguageEnglish
Published United States 20.11.2020
Subjects
Chemistry
Catalysis
Molecular Inorganic Chemistry
Organic Synthesis
Online AccessGet full text

Cover

More Information
Summary: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 )-H activation has been disclosed. This approach provides an efficient platform for rapid access to a privileged library of CF -containing iminoisoindolinones and polyamides by utilizing challenging CF -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.
ISSN:2589-0042