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- Title
From a Fluorenyl Substituted Ylide‐Functionalized Phosphine to a Neutral Phosphide via P−C Bond Cleavage.
- Authors
Löffler, Julian; Gessner, Viktoria H.
- Abstract
Bulky ylide‐substituted phosphines have recently found application as potent ligands in homogeneous catalysis. The attempted synthesis of the ylide‐substituted fluorenylphosphine YPhP(Cy)Flu [YPh=Cy3P(Ph)C; Flu=9‐methylfluorenyl] now resulted in the unexpected elimination of 9‐methylenefluorene during the deprotonation step of the intermediary α‐phosphino phosphonium salt to yield the secondary ylide‐substituted phosphine YPhP(Cy)H. This phosphine underwent formal H2 elimination under basic conditions to form a cyclic phosphonium ylide with a P−C−P−C four‐membered ring via deprotonation of one cyclohexyl group of the PCy3 moiety. Upon coordination to transition metals the secondary ylidylphosphine forms a neutral phosphide ligand by shift of the proton into the ylide‐backbone and formation of zwitterionic metal complexes.
- Subjects
SCISSION (Chemistry); PHOSPHONIUM compounds; PHOSPHINE; PHOSPHIDES; SCRAP metals; HOMOGENEOUS catalysis; METAL complexes; ZWITTERIONS
- Publication
ChemPlusChem, 2023, Vol 88, Issue 5, p1
- ISSN
2192-6506
- Publication type
Article
- DOI
10.1002/cplu.202200459