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Synlett 2018; 29(13): 1759-1764
DOI: 10.1055/s-0037-1610027
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© Georg Thieme Verlag Stuttgart · New York

Selective Synthesis of Carbonates from Glycerol, CO2, and Alkyl Halides Using tert-Butyltetramethylguanidine

Masatoshi Mihara*
a   Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: mihara@omtri.or.jp
,
Kaname Moroga
b   Faculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan
,
Tetsuo Iwasawa
b   Faculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan
,
Takeo Nakai
a   Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: mihara@omtri.or.jp
,
Takatoshi Ito
a   Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: mihara@omtri.or.jp
,
Toshinobu Ohno
a   Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: mihara@omtri.or.jp
,
Takumi Mizuno
a   Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan   Email: mihara@omtri.or.jp
› Author AffiliationsThis work was supported by JSPS KAKENHI Grant Number 25410197 and the Daicel Award in Synthetic Organic Chemistry, Japan.
Further Information

Publication History

Received: 16 March 2018

Accepted after revision: 30 April 2018

Publication Date:
12 July 2018 (online)

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Abstract

Herein, we describe the guanidine-promoted synthesis of carbonates from glycerol, CO2, and alkyl halides. Specifically, a linear tricarbonate (1,2,3-tri-O-butoxycarbonylglycerol), a dicarbonate [butyl (2-oxo-1,3-dioxolan-4-yl)methyl carbonate] containing a linear and a cyclic moiety, and a cyclic monocarbonate (4-hydroxymethyl-2-oxo-1,3-dioxolan) were selectively obtained in good yields, which were strongly affected by the steric bulkiness of the guanidine group substituents. The developed method exhibits the advantages of high efficiency and mild conditions, thus being a powerful tool for the synthesis of value-added products from industrial by-products.

Key words

carbon dioxide - glycerol - carbonates - guanidines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610027.
  • Supporting Information
 

  • References and Notes

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