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Use of a Traceless Activating and Directing Group for the Construction of Trifluoromethylpyrazoles: One‐Pot Transformation of Nitroolefins and Trifluorodiazoethane
Author(s) -
Chen Zhen,
Zheng Yan,
Ma JunAn
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700955
Subject(s) - aromatization , regioselectivity , nitro , group (periodic table) , chemistry , transformation (genetics) , combinatorial chemistry , functional group , stereochemistry , organic chemistry , catalysis , biochemistry , alkyl , polymer , gene
We disclose an efficient one‐pot transformation of trifluorodiazoethane and higher perfluorinated homologues with various nitroolefins. This method takes advantage of the nitro group as a traceless activating and directing group (TADG) that is released in the aromatization step to produce 4‐substituted 3‐perfluoroalkyl pyrazoles with complete regioselectivity. The potential of this method is further demonstrated by the synthesis of penthiopyrad.