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Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400
Synthesis ( IF 2.2 ) Pub Date : 2017-08-28 , DOI: 10.1055/s-0036-1589095
Felipe Demidoff 1 , Fabrícia de Souza 1 , Chaquip Netto 1
Affiliation  

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.

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.



中文翻译:

在PEG-400中通过Heck反应合成Stilbene-醌杂化物

专用于圣保罗RR科斯塔教授在他的67之际生日

抽象的

苯乙烯在90°C下在PEG-400中与3-碘代异黄酮偶联,通过Heck反应立体选择性地导入(E)-二苯乙烯-醌杂化物。发现最佳的反应条件是在90℃下使用NaOH(3当量)和10mol%的乙酸钯15分钟。使用带有吸电子基团的苯乙烯的Heck反应的化学收率(65-98%)大于在芳环上带有给电子基团的苯乙烯的化学收率(7-32%)。特别是,涉及到硝基苯乙烯的Heck反应的化学收率是​​最好的。

苯乙烯在90°C下在PEG-400中与3-碘代异黄酮偶联,通过Heck反应立体选择性地导入(E)-二苯乙烯-醌杂化物。发现最佳的反应条件是在90℃下使用NaOH(3当量)和10mol%的乙酸钯15分钟。使用带有吸电子基团的苯乙烯的Heck反应的化学收率(65-98%)大于在芳环上带有给电子基团的苯乙烯的化学收率(7-32%)。特别是,涉及到硝基苯乙烯的Heck反应的化学收率是​​最好的。

更新日期:2017-08-28
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