| Au(Ⅰ)-Catalyzed Annulation of Benzofurazan N-oxides with Ynamides: From Predicting the Chemo-Selectivity to the Synthesis of 7-Nitroindole Derivatives |
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| 作者姓名： | Changlei Zhu Luyao Kou Xiaoguang Bao |
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| 作者单位： | College of Chemistry |
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| 基金项目： | We are grateful to the National Natural Science Foundation of China(21973068);the project of scientific and technologic infra-structure of Suzhou(SZS201708);the Priority Academic Pro-gram Development of Jiangsu Higher Education Institutions(PAPD)for financial support.The computational resources utilized in this research were provided by Shanghai Supercomputer Center. |
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| 摘 要： | Summaryof main observation and conclusion It could be proposed that gold(I)-catalyzed reactions of ynamides with benzofurazan N-oxidesmightproceed through eitherO-attack or N-attack to affordα-oxo orα-imino Au(I)-carbenoidintermediates.Computational studies were performed to predict that benzofurazan N-oxides are ready to undergo the chemoselective N-attack tothe Au(I)-activatedynamides to generate theα-imino Au(I)-carbenoid intermediate.Experimental studies were carried out to confirm the computational results and the 7-nitroindole derivatives were synthesized in a concise and efficient manner.The unfavored O-attack for benzofurazan N-oxides,which is in contrast to nitrones and pyridine/quinoline N-oxides,in the Au(I)-catalyzed reactions with ynamides is rationalized.
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| 关 键 词： | oxides CATALYZED INDOLE |
Au(I)‐Catalyzed Annulation of Benzofurazan N‐oxides with Ynamides: From Predicting the Chemo‐Selectivity to the Synthesis of 7‐Nitroindole Derivatives |
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| Changlei Zhu,Luyao Kou,Xiaoguang Bao.Au(I)‐Catalyzed Annulation of Benzofurazan N‐oxides with Ynamides: From Predicting the Chemo‐Selectivity to the Synthesis of 7‐Nitroindole Derivatives[J].Chinese Journal of Chemistry,2020,38(1):57-62. |
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| Authors: | Changlei Zhu Luyao Kou Xiaoguang Bao |
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| Abstract: | It could be proposed that gold(I)‐catalyzed reactions of ynamides with benzofurazan N‐oxides might proceed through either O‐attack or N‐attack to afford α‐oxo or α‐imino Au(I)‐carbenoid intermediates. Computational studies were performed to predict that benzofurazan N‐oxides are ready to undergo the chemoselective N‐attack to the Au(I)‐activated ynamides to generate the α‐imino Au(I)‐carbenoid intermediate. Experimental studies were carried out to confirm the computational results and the 7‐nitroindole derivatives were synthesized in a concise and efficient manner. The unfavored O‐attack for benzofurazan N‐oxides, which is in contrast to nitrones and pyridine/quinoline N‐oxides, in the Au(I)‐catalyzed reactions with ynamides is rationalized. |
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