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Synlett 2021; 32(08): 838-844
DOI: 10.1055/a-1335-7330
DOI: 10.1055/a-1335-7330
letter
The Use of 5-Hydroxymethylfurfural towards Fine Chemicals: Synthesis and Direct Arylation of 5-HMF-Based Oxazoles
This research was partly funded by CNPq and CAPES through a PrInt scholarship granted to RdR.
Abstract
5-Hydroxymethylfurfural (5-HMF) is a renewable platform chemical used as a source for obtaining diverse fine chemicals. In this letter, we report the synthesis of 5-HMF-based oxazole compounds. While 5-HMF could be easily converted into the oxazole derivative through the Van Leusen reaction, the direct arylation step needed to access the final compounds was problematic at first. After optimization, a palladium-catalyzed procedure has been developed and used for the synthesis of a series of 33 derivatives. This article reports an extension of the late-stage CH arylation reaction as an application to the oxazole platform derived from biosourced 5-HMF. The challenges in the preparation of the derivatives containing some electron-withdrawing substituents were overcome by the use of a palladium-free method.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1335-7330.
- Supporting Information
Publication History
Received: 24 September 2020
Accepted after revision: 11 December 2020
Accepted Manuscript online:
11 December 2020
Article published online:
02 March 2021
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