Premium
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.