Au(I)‐Catalyzed Annulation of Benzofurazan N‐oxides with Ynamides: From Predicting the Chemo‐Selectivity to the Synthesis of 7‐Nitroindole Derivatives
CHINESE JOURNAL OF CHEMISTRY(2020)
摘要
Summary of main observation and conclusion 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 alpha-oxo or alpha-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 alpha-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
Gold-Catalyzed Reactions,Metal-Catalyzed Reactions
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