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

Koji Hirano; Hideki Yorimitsu; Koichiro Oshima

doi:10.1021/ol048069p

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

Org Lett. 2004 Dec 23;6(26):4873-5. doi: 10.1021/ol048069p.

Authors

Koji Hirano¹, Hideki Yorimitsu, Koichiro Oshima

Affiliation

¹ Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.

PMID: 15606088
DOI: 10.1021/ol048069p

Abstract

[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.