Magnesium-Mediated Regioselective Additions of Bromoform to Quinone Methides and Aurone-Derived Azadienes

Synthesis Pub Date : 2024-07-25 DOI:10.1055/a-2353-1722
Deepak Kumar, Nishikant Satam, Irishi N. N. Namboothiri
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Abstract

The magnesium-mediated addition of bromoform to conjugated electron-deficient alkenes and imines, such as para-quinone methides (p-QMs) and aurone-derived azadienes, respectively, is reported here for the first time. While p-QMs undergo exclusive and hitherto unreported 1,6-addition of bromoform to afford benzylic tribromomethylated diarylmethanes, aurone-derived azadienes undergo both 1,2- and 1,4-additions to furnish α- and γ-tribromomethylamines. A mechanism involving the intermediacy of the tribromomethyl radical has been proposed based on control experiments and EPR studies. Representative synthetic transformations have also been carried out.

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镁介导的溴甲烷与醌甲醚和曙红衍生二氮苯的区域选择性加成反应
本文首次报道了镁介导的溴甲烷与共轭缺电子烯类和亚胺(如对位醌甲酰胺(p-QMs)和源于醛的偶氮)的加成反应。对醌甲烷只经过溴甲烷的 1,6 加成,从而得到苄基三溴甲基化二芳基甲烷,而脲衍生的偶氮二烯则经过 1,2- 和 1,4- 加成,从而得到 α- 和 γ-三溴甲基胺。根据对照实验和 EPR 研究,提出了一种涉及三溴甲基自由基中间体的机制。此外,还进行了具有代表性的合成转化。
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