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Tributylgermanium Hydride as a Replacement for Tributyltin Hydride in Radical Reactions

Tributylgermanium Hydride as a Replacement for Tributyltin Hydride in Radical Reactions

W Russell Bowman, Sussie L Krintel, Mark B Schilling

Org Biomol Chem. 2004 Feb 21;2(4):585-92.

PMID: 14770238

Abstract:

Tributylgermanium hydride (Bu(3)GeH) can be used as an alternative to tributyltin hydride (Bu(3)SnH) as a radical generating reagent with a wide range of radical substrates. Tributylgermanium hydride has several practical advantages over tributyltin hydride, e.g. low toxicity, good stability and much easier work-up of reactions. The reagent can be easily prepared in good yield and stored indefinitely. Suitable substrates include iodides, bromides, activated chlorides, phenyl selenides, tert-nitroalkanes, thiocarbonylimidazolides and Barton esters. Alkyl, vinyl and aryl radicals can be generated in radical reactions including reduction and cyclisation processes. Common radical initiators such as ACCN and triethylborane can be used. The slower rate of hydrogen abstraction by carbon-centred radicals from Bu(3)GeH as compared to Bu(3)SnH facilitates improved cyclisation yields. Polarity reversal catalysis (PRC) with phenylthiol can be used in reactions which generate stable radical intermediates which will not abstract hydrogen from Bu(3)GeH.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP998390	Tributylgermanium hydride		998-39-0	Price

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