Palladium-catalyzed synthesis of 1-alkylphosphonium salts from 1-alkenes

Mieko Arisawa, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

A palladium(0) complex catalyzes the addition reaction of a triarylphosphine and a protic acid to a 1-alkene, giving a 1-alkylphosphonium salt. The treatment of atmospheric ethylene, triphenylphosphine, and (CF3SO2)2NH in the presence of Pd2(dba)3·CHCl3 (dba = dibenzylideneacetone) (0.1 mol %) in chlorobenzene at 65 °C for 5 h gave ethylphosphonium salt in 98% isolated yield. The anti-Markovnikov adduct 1-propylphosphonium salt was obtained by the reaction of atmospheric propene in 95% yield. 1-Butene was converted to 1-butylphosphonium salt in 92% yield in the presence of 1 mol % catalyst. This reaction competed with olefin isomerization, and a mixture of 2-butene and 1-butene (>20:1) was recovered. The reactions of 1-pentene and 1-hexene with triphenylphosphine gave modest yields of the products. The less reactive 1-alkenes, however, reacted effectively with tris(p-chlorophenyl)phosphine. The inner olefins, 2- and 3-pentene also gave a 1-pentylphosphonium salt in high yields via rapid olefin migration.

Original languageEnglish
Pages (from-to)50-51
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number1
DOIs
Publication statusPublished - 2006 Jan 11

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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