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首页> 外文期刊>Chemistry: A European journal >Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: Mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives
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Ruthenium-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes through C-H/N-H activation: Mechanism study and synthesis of dibenzo[a,g]quinolizin-8-one derivatives

机译：通过C-H / N-H活化的钌催化的异喹啉酮与炔烃的氧化偶合/环化：二苯并[a，g]喹啉锌8-一衍生物的机理研究与合成

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The mechanism of [{RuCl _2(p-cymene)} _2]-catalyzed oxidative annulations of isoquinolones with alkynes was investigated in detail. The first step is an acetate-assisted C-H bond activation process to form cyclometalated compounds. Subsequent mono-alkyne insertion of the Ru-C bonds of the cyclometalated compounds then takes place. Finally, oxidative coupling of the C-N bond of the insertion compounds occurs to afford Ru 0 sandwich complexes that undergo oxidation to regenerate the catalytically active Ru ~(II) complex with the copper oxidant and release the desired dibenzo[a,g]quinolizin-8-one derivatives. All of the relevant intermediates were fully characterized and determined by single crystal X-ray diffraction analysis. The [{RuCl _2(p-cymene)} _2]-catalyzed C-H bond functionalization of isoquinolones with alkynes to synthesize dibenzo[a,g]quinolizin-8-one derivatives through C-H/N-H activation was also demonstrated. All in the detail: A detailed study of the mechanism of the Ru ~(II)-catalyzed oxidative coupling/cyclization of isoquinolones with alkynes is reported (see scheme). All of the key stages were identified and intermediates were determined by X-ray crystallography. An efficient and highly regioselective [{RuCl _2(p-cymene)} _2]-catalyzed oxidative annulation of isoquinolones with alkynes to synthesize dibenzo[a,g]quinolizin-8- one derivatives with a broad substrate scope was also developed.
机译：详细研究了[{RuCl _2（p-cymene）} _2]催化异喹诺酮与炔烃氧化环化反应的机理。第一步是乙酸盐辅助的C-H键活化过程，以形成环金属化化合物。随后发生环金属化化合物的Ru-C键的单炔插入。最后，发生插入化合物的CN键的氧化偶联，以提供Ru 0夹心复合物，该复合物经过氧化以与铜氧化剂再生催化活性的Ru〜（II）络合物并释放出所需的二苯并[a，g]喹诺嗪-8一衍生物。所有相关中间体均已通过单晶X射线衍射分析进行了全面表征和测定。还证明了[{RuCl _2（p-cymene）} _2]催化异喹诺酮与炔烃的C-H键官能化，以通过C-H / N-H活化合成二苯并[a，g]喹诺嗪-8-衍生物。所有细节：报道了Ru〜（II）催化异喹诺酮与炔烃的氧化偶联/环化机理的详细研究（参见方案）。确定了所有关键阶段，并通过X射线晶体学确定了中间体。还开发了一种高效且高度区域选择性的[{RuCl _2（p-cymene）} _2]催化的异喹诺酮与炔烃的氧化环化反应，以合成具有广泛底物范围的二苯并[a，g]喹啉嗪-8-一种衍生物。

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