Efficient stereo- and regioselective hydroxylation of alkanes catalysed by a bulky polyoxometalate

Keigo Kamata, Kazuhiro Yonehara, Yoshinao Nakagawa, Kazuhiro Uehara, Noritaka Mizuno

Research output: Contribution to journalArticlepeer-review

227 Citations (Scopus)

Abstract

Direct functionalization of alkanes by oxidation of C-H bonds to form alcohols under mild conditions is a challenge for synthetic chemistry. Most alkanes contain a large number of C-H bonds that present difficulties for selectivity, and the oxidants employed often result in overoxidation. Here we describe a divanadium-substituted phosphotungstate that catalyses the stereo- and regioselective hydroxylation of alkanes with hydrogen peroxide as the sole oxidant. Both cyclic and acyclic alkanes were oxidized to form alcohols with greater than 96% selectivity. The bulky polyoxometalate framework of the catalyst results in an unusual selectivity that can lead to the oxidation of secondary rather than the weaker tertiary C-H bonds. The catalyst also avoids wasteful decomposition of the stoichiometric oxidant, which can result in the production of hydroxyl radicals and lead to non-selective oxidation and overoxidation of the desired products.

Original languageEnglish
Pages (from-to)478-483
Number of pages6
JournalNature Chemistry
Volume2
Issue number6
DOIs
Publication statusPublished - 2010 Jun
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Fingerprint Dive into the research topics of 'Efficient stereo- and regioselective hydroxylation of alkanes catalysed by a bulky polyoxometalate'. Together they form a unique fingerprint.

Cite this