From Stable PH-Ylides to α-Carbanionic Phosphines as Ligands for Zwitterionic Catalysts.

ABSTRACT: Although ylides are commonly used reagents in organic synthesis, the parent methylphosphine MePH₂ only exists in its phosphine form in the condensed phase. Its ylide tautomer H₃ P⁺ -CH₂ ^- is considerably higher in energy. Here, we report on the formation of bis(sulfonyl)methyl-substituted phosphines of the type (RO₂ S)₂ C(H)-PR_2, which form stable PH ylides under ambient conditions, amongst the first examples of an acyclic phosphine which only exists in its PH ylide form. Depending on the exact substitution pattern the phosphines form an equilibrium between the PH ylide and the phosphine form or exist as one of both extremes. These phosphines were found to be ideal starting systems for the facile format

SUBMITTER: Zur JA 

PROVIDER: S-EPMC9401067 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature