Synthesis
DOI: 10.1055/s-0036-1589095
paper
© Georg Thieme Verlag Stuttgart · New York

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

Felipe C. Demidoff, Fabrícia P. de Souza, 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
Financial supports from Brazilian agencies CNPq (Project 442337/2014-0), FAPERJ (Project E-26/111.358/2014), and UFRJ are acknowledged.
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Publication History

Received: 17 May 2017

Accepted after revision: 17 July 2017

Publication Date:
28 August 2017 (eFirst)

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

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