Novel solid networks containing Sn–H as a greener replacement for soluble alkyl Sn–H reagents in radical assisted organic synthesis

Abstract

DiGrignard reagents of the form XMg(CH₂)_nMgX, where X = Br or I and n = 6, 8, 10 or 12, were allowed to react with PhSnCl₃ to produce highly cross-linked Ph–Sn polymeric networks. The Sn–H moiety was incorporated into these insoluble network polymers by treatment with Br₂ and NaBH₄. Excellent accessibility of the Sn–H was displayed by these solvent penetrable but insoluble networks, giving them higher Sn–H loadings than all previously reported supported reagents. These reagents were totally regenerable in NaBH₄ for radical assisted organic synthesis and no detectable leaching of the Sn into solution was observed during these reactions.