Organic letters

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

K Hirano, H Yorimitsu, K Oshima

Index: Hirano, Koji; Yorimitsu, Hideki; Oshima, Koichiro Organic Letters, 2004 , vol. 6, # 26 p. 4873 - 4875

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Citation Number: 26

Abstract

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.