Trifluoromethyl Radical Triggered Radical Cyclization of N-Benzoyl Ynamides leading to Isoindolinones

Maud Cassé (1) , Christian Nisole (1) , Héloïse Dossmann (2, 3) , Yves Gimbert (4, 2, 3) , Jean-Marie Fourquez (1) , Laure Haberkorn (1) , Ollivier Cyril (2, 5) , Fensterbank Louis (2, 5)

1 IRS - Institut de Recherches SERVIER
2 IPCM - Institut Parisien de Chimie Moléculaire
3 CSOB - Chimie Structurale Organique et Biologique
4 UGA [2016-2019] - Université Grenoble Alpes [2016-2019]
5 MACO - Méthodes et Application en Chimie Organique

Under photocatalytic reductive conditions, trifluoromethyl radical addition onto an ynamide followed by cyclization on a benzoyl moiety produces diverse isoindolinone platforms with good yields. The selectivity of the radical cyclization, N-benzoyl vs. N-benzyl as radical acceptor and the E/Z ratio of isomers have been rationalized by modeling.

Mots clés: radical; photoredox chemistry; ynamide

Domaines: Catalyse

Maud Cassé, Christian Nisole, Héloïse Dossmann, Yves Gimbert, Jean-Marie Fourquez, et al.. Trifluoromethyl Radical Triggered Radical Cyclization of N-Benzoyl Ynamides leading to Isoindolinones. Science China Chemistry, 2019, 62, pp.1542-1546. ⟨10.1007/s11426-019-9627-x⟩. ⟨hal-02616094⟩