Synlett 2019; 30(16): 1919-1923
DOI: 10.1055/s-0037-1611917
letter
© Georg Thieme Verlag Stuttgart · New York

Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen

Ryoya Takakura
,
Kazuho Ban
,
Hironao Sajiki
,
This study was supported by a Grant-in-Aid for JSPS Research Fellows from the Japan Society for the Promotion of Science (JSPS, Number: 18J23126) for R.T.
Further Information

Publication History

Received: 12 July 2019

Accepted after revision: 08 August 2019

Publication Date:
27 August 2019 (online)

Abstract

A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.

Supporting Information

 
  • References and Notes

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  • 24 Analysis by atomic absorption spectrometry indicated that no Pt metal (<1 ppm) leached into the reaction mixture during the first run (Table 1, entry 11). When recovered Pt/C was used in a second run, 2a was obtained in 77% yield together with the starting material 1a (11% yield).