On the rapid oxidation of allene-containing phosphines

Feng Cai, Neela D. Thangada, Ende Pan, Joseph M. Ready

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Allene-containing phosphines have recently been shown to serve as effective ligands in transition metal-catalyzed enantioselective reactions. Surprisingly, (2-allenylphenyl)diphenyl phosphines rapidly oxidize when exposed to air, whereas many other triaryl phosphines are stable under ambient conditions. Here we describe experiments designed to understand the origin of this behavior. Stereochemical probes and an isolated phosphonium complex support the hypothesis that phosphines can cyclize onto pendant allenes and that the resultant zwitterion undergoes rapid oxidation with molecular oxygen.

Original languageEnglish (US)
Pages (from-to)5619-5622
Number of pages4
JournalOrganometallics
Volume32
Issue number19
DOIs
StatePublished - Oct 14 2013

Fingerprint

Phosphines
phosphines
Oxidation
oxidation
zwitterions
Molecular oxygen
Transition metals
transition metals
Ligands
ligands
propadiene
probes
air
oxygen
Air
Experiments

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

On the rapid oxidation of allene-containing phosphines. / Cai, Feng; Thangada, Neela D.; Pan, Ende; Ready, Joseph M.

In: Organometallics, Vol. 32, No. 19, 14.10.2013, p. 5619-5622.

Research output: Contribution to journalArticle

Cai, Feng ; Thangada, Neela D. ; Pan, Ende ; Ready, Joseph M. / On the rapid oxidation of allene-containing phosphines. In: Organometallics. 2013 ; Vol. 32, No. 19. pp. 5619-5622.
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