Development of Environmentally Friendly Methods for Organic Synthesis based on Design and Preparation of Less Toxic Organotin Reagents

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Organotin reagents are valuable for fine organic synthesis. However, tributyltin compounds, frequently used for this purpose, have high toxicity with difficulty of decomposition and separation. To overcome these weaknesses, we studied synthesis and synthetic use of benzyltin compounds. Tribenzylstannane (Bn_3SnH) was found to be useful for radical reduction of organic halides. The tin byproducts (Bn_3SnX) are easily separable by filtration and silica gel column chromatography and decomposable by treatment with basic hydrogen peroxide.