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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 
 
 

Boron trifluoride-mediated alkylation of diphenylphosphine with tert-alkyl fluoride.

[reaction: see text] Treatment of tertiary alkyl fluoride with diphenylphosphine in the presence of a stoichiometric amount of boron trifluoride etherate yields the corresponding tert-alkyldiphenylphosphine despite the coexistence of the strong Lewis acid and the highly coordinating phosphine. Use of diphenyl(trimethylsilyl)phosphine as a nucleophile makes the reaction catalytic in boron trifluoride.[1]

References

  1. Boron trifluoride-mediated alkylation of diphenylphosphine with tert-alkyl fluoride. Hirano, K., Yorimitsu, H., Oshima, K. Org. Lett. (2004) [Pubmed]
 
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