C-Alkynylation of Chromones by Sonogashira Reaction

Tamás Patonay; István Pazurik; Anita Ábrahám

doi:10.1071/CH13006

RESEARCH ARTICLE

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C-Alkynylation of Chromones by Sonogashira Reaction

Tamás Patonay ^A ^C , István Pazurik ^B and Anita Ábrahám ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Organic Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.

^B Research Group of Homogeneous Catalysis HAS-UD, Egyetem tér 1, H-4032 Debrecen, Hungary.

^C Corresponding author. Email: patonay.tamas@science.unideb.hu

Australian Journal of Chemistry 66(6) 646-654 https://doi.org/10.1071/CH13006
Submitted: 10 January 2013 Accepted: 7 February 2013 Published: 24 April 2013

Abstract

Sonogashira reaction of bromochromones and -flavones with a bromine atom on their benzene or heterocyclic ring with various terminal alkynes gave the desired products with nearly the same efficiency as the previously used iodine derivatives. The coupling reactions were performed in the presence of [tetrakis(triphenylphosphine)palladium(0)], copper(i) co-catalyst, and triethylamine, resulting in the formation of numerous hitherto unknown alkynylated oxygen heterocycles, and provide further proof for the applicability of this reaction for these O-heterocycles. Chromones with ethynyl functionality were prepared by removal of the trimethylsilyl protecting group and used as terminal alkynes in a second cross-coupling reaction.

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C-Alkynylation of Chromones by Sonogashira Reaction

Abstract

References

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