Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

Felipe C. Demidoff; Fabrícia P. de Souza; Chaquip D. Netto

doi:10.1055/s-0036-1589095

Synthesis, Table of Contents

Synthesis 2017; 49(23): 5217-5223
DOI: 10.1055/s-0036-1589095

paper

Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

Felipe C. Demidoff

Laboratório de Química, Universidade Federal do Rio de Janeiro, Campus Professor Aloísio Teixeira, Macaé, RJ 27930-560, Brazil Email: chaquip@gmail.com

,

Fabrícia P. de Souza

Laboratório de Química, Universidade Federal do Rio de Janeiro, Campus Professor Aloísio Teixeira, Macaé, RJ 27930-560, Brazil Email: chaquip@gmail.com

,

Chaquip D. Netto*

Laboratório de Química, Universidade Federal do Rio de Janeiro, Campus Professor Aloísio Teixeira, Macaé, RJ 27930-560, Brazil Email: chaquip@gmail.com

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Abstract

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Dedicated to Professor Paulo R. R. Costa on the occasion of his 67^th birthday

Abstract

Styrenes were coupled with 3-iodolawsone in PEG-400 at 90 °C, leading stereoselectively to (E)-stilbene-quinone hybrids through Heck reactions. The best reaction conditions were found to be the use of NaOH (3 equiv) and 10 mol% of palladium acetate at 90 °C for 15 minutes. The chemical yields of the Heck reactions using styrenes with electron-withdrawing groups (65–98%) were greater than styrenes bearing electron-donating groups (7–32%) on the aromatic ring. In particular, the chemical yields of Heck reactions involving nitrostyrenes were the best ones observed.

Key words

Heck reaction - PEG-400 - Wittig reaction - styrenes - naphthoquinones - stilbenes - 3-iodolawsone

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References

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