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A Cascade Approach to Captodative Trifluoromethylated Enamines or Vinylogous Guanidinium Salts: Aromatic Substituents as Switches of Reaction Direction
Author(s) -
Rulev Alexander Yu.,
Muzalevskiy Vasiliy M.,
Kondrashov Evgeniy V.,
Ushakov Igor A.,
Shastin Aleksey V.,
Balenkova Elizabeth S.,
Haufe Günter,
Nenajdenko Valentine G.
Publication year - 2010
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.200900926
Subject(s) - chemistry , trifluoromethyl , nucleophile , nucleophilic addition , trifluoromethylation , cascade , nucleophilic aromatic substitution , fluorine , enamine , medicinal chemistry , organic chemistry , nucleophilic substitution , alkyl , catalysis , chromatography
β‐Halo‐β‐(trifluoromethyl)styrenes readily react with a variety of nitrogen nucleophiles bearing primary amino groups to afford either the captodative trifluoromethylated enamines or vinylogous guanidinium salts in a selective fashion depending on the electronic natures of the aromatic substituents.