This work reports gold-catalyzed bicyclic annulations of 2-alkynyl-1-carbonylbenzenes with vinyldiazo ketones that serve as five-atom building units. The importance of these reactions is to access 4,5-dihydro-benzo[g]indazoles, which form the structural cores of various bioactive molecules. According to our mechanistic analysis, we postulate initial [5+4]-cycloadditions between benzopyrilium intermediates and vinyldiazo ketones, followed by 6-π-electrocyclizations to achieve the excellent stereoselectivity.
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