The room temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate, [bmim][PF6], is used as a 'green' recyclable alternative to dipolar aprotic solvents for the regioselective alkylation at the heteroatom of indole and 2-naphthol.
Earle, Martyn J.,McCormac, Paul B.,Seddon, Kenneth R.
p. 2245 - 2246
(2007/10/03)
Influence of phase transfer catalyst structure on selectivity
A concise review is given of systematic studies concerned with the tuning of regio-, "frequentio-", chemo-, and diastereoselectivity by the structure or type of phase transfer catalyst. - Keywords: phase transfer catalysis; regioselectivity; selectivity control; stereoselectivity; C/O-alkylation; C/N-alkylation.
Dehmlow, E. V.
p. 1998 - 2005
(2007/10/03)
HIGHLY SELECTIVE BENZILATIONS OF β-NAPHTHOXIDE ANION IN HETEROGENEOUS MEDIA
Each of the four products resulting from the benzylation of the ambident β-naphthoxide anion can be efficiently and selectively obtained in mild an economical conditions by a judicious choice of the solid base: LiOH, LiOtBu or KOH-Aliquat.
Bram, G.,Loupy, A.,Sansoulet, J.,Vaziri-Zand, F
p. 5035 - 5038
(2007/10/02)
Regioselectivity of the Alkylation of Ambident Anionic Species on Alumina or in the Presence of 'Solid Hexamethylphosphoric Triamide'
C-Alkylation of the acetoacetate anions and of sodium naphthoxide is highly favoured on alumina, while O-alkylation of the acetoacetate anion predominates in tetrahydrofuran in the presence of solid hexamethylphosphoric triamide.