TY - JOUR
T1 - Ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoro-methanesulfonyl)imide, resulted in the first catalyst-free aminohalogenation of electron-deficient alkenes
AU - Wang, Yi-Ning
AU - Ni, Bukuo
AU - Headley, Allan D.
AU - Li, Guigen
PY - 2007/2
Y1 - 2007/2
N2 - 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(SO2CF3) 2]}. [Bmim][N(SO2CF3)2] was found to be superior not only to classical organic solvents but also to its counterpart, [bmim][BF4], 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-NsNCl2 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%).
AB - 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(SO2CF3) 2]}. [Bmim][N(SO2CF3)2] was found to be superior not only to classical organic solvents but also to its counterpart, [bmim][BF4], 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-NsNCl2 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%).
KW - α,β-unsaturated ketones
KW - Aminohalogenation
KW - Haloamines
KW - Ionic liquids
UR - http://www.scopus.com/inward/record.url?scp=34547208019&partnerID=8YFLogxK
U2 - 10.1002/adsc.200600277
DO - 10.1002/adsc.200600277
M3 - Article
SN - 1615-4150
VL - 349
SP - 319
EP - 322
JO - Advanced Synthesis & Catalysis
JF - Advanced Synthesis & Catalysis
IS - 3
ER -