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Synthesis 2023; 55(23): 4000-4010
DOI: 10.1055/a-2147-2788
paper

Application of the Heck Reaction for the Synthesis of C-Glycosyl Phenolic Compounds

Sara M. Tomé
a   LAQV-REQUIMTE & Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
,
Raquel G. Soengas  ∗
b   Department of Organic and Inorganic Chemistry, University of Oviedo, 33006 Oviedo, Spain
,
Artur M. S. Silva  ∗
a   LAQV-REQUIMTE & Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
› Author AffiliationsThis work has received financial support from the University of Aveiro, Fundação para a Ciência e a Tecnologia (FCT/MEC; UIDB/50006/2020), and Portugal 2020 (EPIGENGLICON, POCI-01-0145-FEDER-029767), Principado de Asturias (FICYT IDI/2018/000181), Ministerio de Asuntos Económicos y Transformación Digital (MINECO; PID2019-109253RB-I00) and the Fourth Framework Programme (MCIU/AEI/FEDER, UE; RTI2018-099756-B-I00). S.M.T. thanks Fundação para a Ciência e a Tecnologia for her PhD grant (SFRH/BD/103252/2014).
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Abstract

The potential of the Heck reaction for the C-glycosylation of phenolic compounds was explored. An efficient and general methodology for the synthesis of C-glycosylated phenolic compounds based on the Heck coupling of halogenated phenolic derivatives (chromones, 2-styrylchromones, and xanthones) and sugar alkenes was developed. The protocol was applied to the preparation of previously unreported C-glycosylated 2-styrylchromones and xanthones of potential biological relevance.

Key words

Heck reaction - phenolic compounds - chromones - xanthones - 2-styrylchromones - C-glycosylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2147-2788.
  • Supporting Information


Publication History

Received: 12 June 2023

Accepted after revision: 02 August 2023

Accepted Manuscript online:
02 August 2023

Article published online:
19 September 2023

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