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Unprecedented Transformation of a Directing Group Generated In Situ and Its Application in the One‐Pot Synthesis of 2‐Alkenyl Benzonitriles
Author(s) -
Kumar Ravi,
Arigela Rajesh K.,
Kundu Bijoy
Publication year - 2015
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.201501449
Subject(s) - benzonitrile , cyanation , chemistry , catalysis , combinatorial chemistry , in situ , transformation (genetics) , group (periodic table) , olefin fiber , reaction conditions , organic chemistry , medicinal chemistry , biochemistry , gene
An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de‐novo synthesis of 2‐alkenylated benzonitrile derivatives from benzoyl azides through ortho CH activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using 31 P NMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions.