New Polymer-Supported Organosilicon Reagents

Significance

The authors have prepared a series of soluble and insoluble polymer-supported organosilanes. The polymeric thiophene 1, which was prepared by the copolymerization of styrene and 4-(thiophen-2-yl)styrene, was functionalized with various organosilanes by using two different strategies (Routes A and B). For example, allyldimethylsilyl and allyldiphenylsilyl groups were introduced into polymer 1 via route A (82-93% yield) and route B (37-60% yield), respectively. Hydrosilane 2, which was prepared via route A, was used for olefine hydrosilylation. Thus, silane 2 reacted with safrole 7 to give (3-arylpropyl)silane 8. Treatment of 8 with TBAF gave the polymeric thiophene 1 and (3-arylpropyl)silanol 9 which was readily converted into 3-arylpropylalcohol 10 via Tamao-Fleming oxidation.