Palladium‐Catalyzed Enantio‐ and Regioselective Ring‐Opening Hydrophosphinylation of Methylenecyclopropanes

Jian Zhou, Ling Meng, Shujuan Lin, Baohua Cai, Jun (Joelle) Wang*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

8 Citations (Scopus)

Abstract

Transition metal-catalyzed hydrofunctionalization of methylenecyclopropanes (MCPs) has presented a considerable challenge due to the difficult manipulation of regioselectivity and complicated reaction patterns. Herein, we report a straightforward Pd-catalyzed ring-opening hydrophosphinylation reaction of MCPs via highly selective C−C bond cleavage. This method allows for rapid and efficient access to a wide range of chiral allylic phosphine oxides in good yields and high enantioselectivities. Additionally, density functional theory (DFT) calculations were performed to elucidate the reaction mechanism and the origin of enantioselectivity.
Original languageEnglish
Article numbere202303727
Number of pages8
JournalAngewandte Chemie. International Edition
Volume62
Issue number26
Early online date25 Apr 2023
DOIs
Publication statusPublished - 26 Jun 2023

Scopus Subject Areas

  • Chemistry(all)
  • Catalysis

User-Defined Keywords

  • C−C Bond Cleavage
  • C−P Bond Formation
  • DFT Calculations
  • Hydrophosphinylation
  • Phosphine

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