Au(Ⅰ)-Catalyzed Annulation of Benzofurazan N-oxides with Ynamides: From Predicting the Chemo-Selecti

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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 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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