Synfacts 2011(4): 0460-0460  
DOI: 10.1055/s-0030-1259735
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

A Silica-Supported Imidazolium Salt for Nucleophilic Substitution in Water

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
J. Li, J.-j. Cao, J.-f. Wei*, X.-y. Shi, L.-h. Zhang, J.-j. Feng, Z.-g. Chen
Shaanxi Normal University, Xi’an and Lanzhou University, P. R. of China
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Publication History

Publication Date:
18 March 2011 (online)


Nucleophilic substitution of alkyl halides and tosylates with sodium azide and thiocyanate with a silica-supported imidazolium catalyst in water is described. The nucleophilic substitution of benzyl and alkyl halides and tosylates with NaN3 proceeded in water in the presence of the silica-supported imidazolium salt 1 to give the corresponding benzyl and alkyl azides (18 examples). Under similar conditions, nucleophilic substitution with NaSCN led to the corresponding benzyl and alkyl thiocyanates (16 examples).