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Ionic Liquid, 1‐ n ‐Butyl‐3‐methylimidazolium Bis(trifluoromethanesulfonyl)imide, Resulted in the First Catalyst‐Free Aminohalogenation of Electron‐Deficient Alkenes
Author(s) -
Wang YiNing,
Ni Bukuo,
Headley Allan D.,
Li Guigen
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600277
Subject(s) - ionic liquid , imide , chemistry , catalysis , stereoselectivity , halogen , inert gas , medicinal chemistry , metal , organic chemistry , alkyl
The 2‐Ns‐based aminohalogenation of α,β‐unsaturated ketones has been achieved in an ionic liquid, 1‐ n ‐butyl‐3‐methylimidazolium bis(trifluoromethanesulfonyl)imide {[bmim][N(SO 2 CF 3 ) 2 ]}. [Bmim][N(SO 2 CF 3 ) 2 ] was found to be superior not only to classical organic solvents but also to its counterpart, [bmim][BF 4 ], which was proven to be successful in the TsNCl 2 ‐based aminohalogenation but failed to give any product for this reaction. The present process takes the advantage of 2‐NsNCl 2 as the stable nitrogen/halogen source in a one‐pot operation without the use of any metal catalysts, it is convenient to perform without special protection of inert gases. Eight examples were examined with good to excellent stereoselectivity (1:5 to one isomer) and modest to good chemical yields (53–72 %).