用低电势邻醌催化剂替代化学计量的 DDQ，实现药物中间体仲吲哚的有氧脱氢反应。
Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates.
机构信息
Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.
出版信息
Org Lett. 2019 Feb 15;21(4):1176-1181. doi: 10.1021/acs.orglett.9b00111. Epub 2019 Jan 31.
Abstract
A transition-metal/quinone complex, [Ru(phd)] (phd = 1,10-phenanthroline-5,6-dione), is shown to be effective for aerobic dehydrogenation of 3° indolines to the corresponding indoles. The results show how low potential quinones may be tailored to provide a catalytic alternative to stoichiometric DDQ, due to their ability to mediate efficient substrate dehydrogenation while also being compatible with facile reoxidation by O. The utility of the method is demonstrated in the synthesis of key intermediates to pharmaceutically important molecules.
摘要
一种过渡金属/醌配合物[Ru(phd)]（phd = 1,10-菲咯啉-5,6-二酮）被证明可有效地将 3°吲哚啉有氧脱氢为相应的吲哚。结果表明，低势能醌可以通过调节底物的有效脱氢来替代化学计量的 DDQ，同时也可通过 O2 容易地进行再氧化，从而提供一种催化替代方法。该方法在合成具有重要药物作用的分子的关键中间体方面具有广泛的应用。
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