Tetrahedron letters

Borane-induced radical reduction of 1-alkenyl-and 1-alkynyl-λ 3-iodanes with tetrahydrofuran

M Ochiai, Y Tsuchimoto, T Hayashi

Index: Ochiai, Masahito; Tsuchimoto, Yoshimi; Hayashi, Takanori Tetrahedron Letters, 2003 , vol. 44, # 29 p. 5381 - 5384

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Citation Number: 13

Abstract

Exposure of 1-alkenyl (phenyl)-and 1-alkynyl (phenyl)-λ3-iodanes to THF at room temperature in the presence of a catalytic amount of trialkylborane results in smooth reduction to give 1-iodo-1-alkenes and 1-iodo-1-alkynes as major products, respectively. The key step in the reductions probably involves a single-electron transfer from α- tetrahydrofuryl radical to the λ3-iodanes, which generates the labile [9-I-2] iodanyl radicals.