Abstract
Rasta resin-PPh3 BnCl, a new heterogeneous polystyrene-based
phosphonium salt, has been synthesized and used to catalyze cyanosilylation
reactions of aldehydes and ketones. It was found to be more efficient
as a catalyst than a similar heterogeneous phosphonium salt anchored
onto a polystyrene-based on the Merrifield resin architecture of
2% divinylbenzene cross-linking. In these reactions rasta
resin-PPh3 BnCl was separated from the desired reaction
product simply by filtration, and it could be reused without significant
loss of catalytic activity numerous times.
Key words
polymer-supported catalyst - polystyrene - phosphonium
salt - organocatalysis - cyanosilylation
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See Supporting Information for details.
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General Procedure
for Cyanosilylation Reactions
To a solution of the
aldehyde or ketone substrate (0.5 mmol) and TMSCN (0.75 mmol) in
CHCl3 was added 2 or 3 (0.025 mmol). The reaction mixture was
stirred at 50 ˚C until TLC analysis indicated that the
starting material was completely consumed. The reaction mixture
was then filtered and the polymer-supported catalyst was washed
with CH2 Cl2 (2 × 50
mL). The combined filtrate was concentrated in vacuo to afford the
desired product. All products were characterized by MS, ¹ H
NMR, and ¹³ C NMR spectroscopy.