Platinum(II) mediated oxidation of remote CH bonds in functionalized organic molecules

Naomi Basickes, Ayusman Sen

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

The oxidation of remote CH bonds of aliphatic alcohols, carboxylic acids, sulfonic acids and phosphonic acids by the PtII ion in water was examined. The reactions were very specific with respect to the degree of oxidation: only hydroxylation (or its equivalent) was observed and further oxidation to the corresponding aldehyde or carboxylic acid functionally did not occur. The order of reactivity was σ-CH ≪ β-CH < γ-CH < δ-CH for alcohols and σ-CH ≪ β-CH < γ-CH {slanted equal to or greater-than} δ-CH for the acids. The reactions are thought to proceed by the initial coordination of the functional group followed up the formation of an intermediate platinacylce upon CH activation. The observed regioselectivity arises from the tendency to form the metallacycle with the least ring strain. It was possible to make the oxidations catalytic in PtII by the addition of a reoxidant, such as K2PtCl6.

Original languageEnglish (US)
Pages (from-to)197-202
Number of pages6
JournalPolyhedron
Volume14
Issue number1
DOIs
StatePublished - Jan 1995

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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