Tributylgermanium hydride

Again, the reaction could be effected with tributyltin hydride, tris(trimethylsilyl)silane and tributylgermanium hydride, though only the product of reduction, 166, was given with samarium(II) iodide. A similar outcome was noted for dihydroazastilbene 169, with the products of reduction 172, or//jo-cyclisation 170, and i/>so-cyclisation and rearrangement 171, each formed in similar quantity (Scheme 47). 

Completing the series, tributylgermanium hydride also reduces acyl chlorides to the aldehydes in the presence of Pd(Ph3P)4, but under more stringent conditions (Scheme The reactions are only effective at 80-100 °C in HMPA. In the case of 20 the product could be fully reduced to phenylpropionaldehyde in 37% yield if 3 equiv of the hydride was used and the reaction temperature was increased to 100 °C. 

Due to the toxicity of tin reagents, Fu developed a method using catalytic amounts of BusSnH that is regenerated by using phenylsilane or polymethylhydrosiloxane (PMHS) in alcoholic solvents (Scheme 8.43). Tributylgermanium hydride can substitute BusSnH in some reaction such as the reduction of arylazides to anilines. ... 

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