Radical Reactions in Aqueous Medium Using (Me₃Si)₃SiH

Al Postigo, Sergey Kopsov, Carla Ferreri and Chryssostomos Chatgilialoglu*

*ISOF, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy, Email: chrysisof.cnr.it

A. Postigo, S. Kopsov, C. Ferreri, C. Chatgilialoglu, Org. Lett., 2007, 9, 5159-5162.

DOI: 10.1021/ol7020803

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Abstract

(Me₃Si)₃SiH was successfully used in various radical-based transformations in water. The system comprising substrate, silane, and initiator (ACCN) mixed in aqueous medium at 100°C worked well for both hydrophilic and hydrophobic substrates. In case of water-soluble water-soluble substrates, an amphiphilic thiol was also needed.

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Key Words

tris(trimethylsilyl)silane, green chemistry, Barton-McCombie reaction, dehalogenations, reduction of azides

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ID: J54-Y2007-3850