Synthesis of 6‐Trifluoromethylphenanthridines through Radical Trifluoromethylation of Isocyanides with Sodium Triflinate under Visible Light | Zendy

Li Jianbin | Zendy; Caiuby Clarice A. D. | Zendy; Paixão Márcio W. | Zendy; Li ChaoJun | Zendy

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Synthesis of 6‐Trifluoromethylphenanthridines through Radical Trifluoromethylation of Isocyanides with Sodium Triflinate under Visible Light

Author(s) -

Li Jianbin,

Caiuby Clarice A. D.,

Paixão Márcio W.,

Li ChaoJun

Publication year - 2018

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201701487

Subject(s) - chemistry , trifluoromethylation , annulation , radical , combinatorial chemistry , hypervalent molecule , photochemistry , organic synthesis , cascade reaction , molecule , organic chemistry , iodine , alkyl , trifluoromethyl , catalysis

Trifluoromethylation enabled by photochemistry enriched the toolbox of synthetic chemists, to allow the simple and efficient installation of CF 3 groups in organic molecules. Herein, we report a cascade addition/annulation reaction of 2‐isocyanobiphenyls towards the synthesis of 6‐trifluoromethylphenanthridines. It is proposed that this reaction is triggered by the CF 3 radical generated from photoexcited 2,3‐butanedione (diacetyl) and sodium triflinate. In contrast to classical aromatic trifluoromethylations, this work does not require any additives and features formation of a C–CF 3 bond with concomitant construction of an aromatic scaffold.

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