Reduction of organic halides with tri-2-furylgermane: Stoichiometric and catalytic reduction

Tri-2-furylgermane proved to be an effective reagent for the radical reduct ion of organic halides. Treatment of 1-bromododecane with tri-2-furylgerman e in THF at 25 degreesC in the presence of a catalytic amount of triethylbo rane afforded dodecane almost quantitatively. Radical cyclization of 2-iodo ethanal allyl acetal afforded five-membered products under the same reactio n conditions. These reactions proceeded with NaBH4 in the presence of a cat alytic amount of germanium hydride. The reaction took place in water as wel l as in THF to give the corresponding reduced compounds in good yields.