Peroxide-Selective Reduction of O2 at Redox-Inactive Rare-Earth(III) Triflates Generates an Ambiphilic Peroxide

J Am Chem Soc. 2022 Sep 21;144(37):17295-17306. doi: 10.1021/jacs.2c08140. Epub 2022 Sep 9.

Abstract

Metal peroxides are key species involved in a range of critical biological and synthetic processes. Rare-earth (group III and the lanthanides; Sc, Y, La-Lu) peroxides have been implicated as reactive intermediates in catalysis; however, reactivity studies of isolated, structurally characterized rare-earth peroxides have been limited. Herein, we report the peroxide-selective (93-99% O22-) reduction of dioxygen (O2) at redox-inactive rare-earth triflates in methanol using a mild metallocene reductant, decamethylferrocene (Fc*). The first molecular praseodymium peroxide ([PrIII2(O22-)(18C6)2(EG)2][OTf]4; 18C6 = 18-crown-6, EG = ethylene glycol, -OTf = -O3SCF3; 2-Pr) was isolated and characterized by single-crystal X-ray diffraction, Raman spectroscopy, and NMR spectroscopy. 2-Pr displays high thermal stability (120 °C, 50 mTorr), is protonated by mild organic acids [pKa1(MeOH) = 5.09 ± 0.23], and engages in electrophilic (e.g., oxygen atom transfer) and nucleophilic (e.g., phosphate-ester cleavage) reactivity. Our mechanistic studies reveal that the rate of oxygen reduction is dictated by metal-ion accessibility, rather than Lewis acidity, and suggest new opportunities for differentiated reactivity of redox-inactive metal ions by leveraging weak metal-ligand binding events preceding electron transfer.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Crown Ethers
  • Esters
  • Ethylene Glycols
  • Ligands
  • Metallocenes
  • Metals / chemistry
  • Methanol
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Peroxides*
  • Phosphates
  • Praseodymium*
  • Reducing Agents

Substances

  • Crown Ethers
  • Esters
  • Ethylene Glycols
  • Ligands
  • Metallocenes
  • Metals
  • Peroxides
  • Phosphates
  • Reducing Agents
  • aza-18-crown-6 ether
  • Praseodymium
  • Oxygen
  • Methanol