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Preparation of 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid catalyzed by iron(III)porphyrins with (diacetoxyiodo)benzene
Bioorganic & Medicinal Chemistry Letters ( IF 2.5 ) Pub Date : 2010-07-21 , DOI: 10.1016/j.bmcl.2010.07.071
Qi-Di Zhong , Yun-Zhou Xue , Hong Yan , Xiu-Qing Song , Ru-Gang Zhong

Using iron(III)porphyrins in combination with (diacetoxyiodo)benzene allows for the conversion of 2,9-bis(bromomethyl)-4,7-diphenyl-1,10-phenanthroline into 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid. This method provides a cost-effective and environmentally-friendly oxidation procedure using less toxic PhI(OAc)2 and biologically relevant iron(III)porphyrins. The catalytic activity of five kinds of iron-metallated functional porphyrins were investigated using different oxidants, including air, H2O2, PhI(OAc)2, PhIO and NaClO. Our results showed that the use of T(p-NO2)PPFeCl with PhI(OAc)2 as the oxidant in the presence of water displays remarkable activity for the desired oxidation reaction. The generality of this method was examined by synthesizing the carboxylic acids of pyridines and quinolines.



中文翻译:

铁(III)卟啉与(二乙酰氧基碘)苯催化制备4,7-二苯基-1,10-菲咯啉-2,9-二羧酸

结合使用铁(III)卟啉与(二乙酰氧基碘)苯可将2,9-双(溴甲基)-4,7-二苯基-1,10-菲咯啉转化为4,7-二苯基-1,10-菲咯啉-2,9-二羧酸。该方法使用毒性较小的PhI(OAc)2和生物学上相关的铁(III)卟啉提供了一种经济高效且对环境友好的氧化程序。利用空气,H 2 O 2,PhI(OAc)2,PhIO和NaClO等不同的氧化剂研究了五种铁金属化的卟啉的催化活性。我们的结果表明,将T(p -NO 2)PPFeCl与PhI(OAc)2一起使用因为氧化剂在水的存在下对于所需的氧化反应显示出显着的活性。通过合成吡啶和喹啉的羧酸来检验该方法的一般性。

更新日期:2010-07-21
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