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Silica‐Bound 3‐{2‐[Poly(ethylene Glycol)]ethyl}‐Substituted 1‐Methyl‐1 H ‐imidazol‐3‐ium Bromide: A Recoverable Phase‐Transfer Catalyst for Smooth and Regioselective Conversion of Oxiranes to β ‐Hydroxynitriles in Water
Author(s) -
Reza Kiasat Ali,
Ayashi Neda,
FallahMehrjardi Mehdi
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200192
Subject(s) - chemistry , regioselectivity , catalysis , ethylene glycol , bromide , selectivity , phase transfer catalyst , ethylene , silica gel , cyanide , polymer chemistry , medicinal chemistry , organic chemistry
A series of β ‐hydroxynitriles were efficiently synthesized from the regioselective ring opening of oxiranes by cyanide anion in the presence of silica‐bound 3‐{2‐[poly(ethylene glycol)]ethyl}‐substituted 1‐methyl‐1 H ‐imidazol‐3‐ium bromide (SiO 2 PEGImBr) as a novel recoverable phase‐transfer catalyst in H 2 O ( Scheme 1 and Table 2 ). The workup procedure was straightforward, and the catalyst could be reused over four times with almost no loss of catalytic activity and selectivity.