Open AccessCatalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4
Author(s) -
Timothy D. Schoch,
Mukulesh Mondal,
Jimmie D. Weaver
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c04305
Subject(s) - chemistry , isomerization , phthalonitrile , carbazole , catalysis , fluorine , combinatorial chemistry , photochemistry , organic chemistry , phthalocyanine
Presented is an economical means of removing fluorine from various highly fluorinated arenes using NaBH 4 . The procedure was adapted for different classes of perfluoroarenes. A novel isomer of an emerging class of organic dyes based on the carbazole phthalonitrile motif was succinctly synthesized in two steps from tetrafluorophthalonitrile, demonstrating the utility of the hydrodefluorination procedure. Initial exploration of the dye shows it to be photoactive and capable of facilitating contrathermodynamic styrenoid E / Z isomerization.