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A Cross‐Dehydrogenative Annulation Strategy towards Synthesis of Polyfluorinated Phenanthridinones with Copper
Author(s) -
Mandal Anup,
Selvakumar Jayaraman,
Dana Suman,
Mukherjee Upasana,
Baidya Mahiuddin
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800337
Subject(s) - annulation , chemistry , regioselectivity , combinatorial chemistry , salt (chemistry) , copper , organic chemistry , catalysis
The first cross‐dehydrogenative annulation of (hetero)aromatic amides with polyfluoro(hetero)arenes is presented. This operationally simple oxidative annulation process is mediated by inexpensive copper salt, accommodates a wide range of substrates with exquisite chemo‐ and regioselectivity profile, and produces demanding polyfluorinated phenanthridinones in high yields (up to 92 %). Using alkenyl amides under identical conditions, the synthesis of polyfluorinated 2‐quinolones has also been accomplished. Given the importance of fluorinated heterocycles in the pharmaceutical industry and drug discovery, this work is highly significant.