One-pot synthesis of 1,2/3-triols from the allylic hydroperoxides catalyzed by zeolite-confined osmium(0) nanoclusters

Goksu H., Dalmizrak D., Akbayrak S., GÜLTEKİN M. S., ÖZKAR S., Metin O.

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, vol.378, pp.142-147, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 378
  • Publication Date: 2013
  • Doi Number: 10.1016/j.molcata.2013.06.013
  • Journal Name: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.142-147
  • Keywords: Zeolite-Y, Osmium nanoclusters, Reusable catalyst, Hydroperoxide, 1,2,3-triols, DIHYDROXYLATION, CONDURITOLS, CYCLITOLS
  • Middle East Technical University Affiliated: Yes

Abstract

A facile, efficient and eco-friendly method for the one-pot synthesis of 1,2/3-triols from the allylic hydroperoxides were developed by using zeolite-confined osmium(0) nanoclusters as reusable catalyst and without using any co-oxidant (H2O2, (BuOOH)-Bu-t, NMO, etc.) in water/acetone (v/v = 1/4) mixture at room temperature. In this method, the oxygen atom of the allylic hydroperoxide group was transferred to the double bond of the same molecule via zeolite-confined osmium(0) nanoclusters. The method has been successfully applied to various allylic hydroperoxides and the corresponding 1,2/3-triols were obtained in high chemical yield. Moreover, a plausible mechanism was proposed for the catalytic oxidation of allylic hydroperoxide to the respective 1,2/3-triols in the presence of zeolite-Os-0 catalyst gathering all the results collected by testing a variety of allylic hydroperoxides in the presence of zeolite-Os-0 catalyst. (c) 2013 Elsevier B.V. All rights reserved.