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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of an Azido-Substituted 8-Membered Ring Laddersiloxane and Its Application in Catalysis
Yujia Liu1, Niyaz Yagafarov1, Koki Shimamura1,2
1Department of Chemistry and Chemical Biology, Graduate School of Science and Technology, Gunma University, 1-5-1 Tenjin-cho, Kiryu 376-8515, Japan.
Abstract:
A first syn-type tricyclic 8-8-8 (three fused-8-membered ring) laddersiloxane functionalized with four azido groups was successfully synthesized through efficient and highly selective hydrosilylation and nucleophilic substitution, achieving an excellent overall yield. The starting material, a tetravinyl-substituted 8-8-8 laddersiloxane, was prepared via a straightforward and scalable method. The obtained azido-functionalized ladder compound, fully characterized, constitutes a versatile building block for hybrid materials. Reacting this compound with 2-ethynylpyridine via click chemistry yielded a multidentate ligand containing four 2-triazole-pyridyl moieties. This N,N-bidentate ligand was subsequently employed in copper-catalyzed alcohol oxidative dehydrogenation reactions, demonstrating its potential in catalysis.
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