TMSOTf-Promoted Intermolecular Cascade Reaction of Aromatic Diazo Ketones with Olefins: Selective Synthesis of
Madhu Babu Tatina1, Wang Xinzhu1, Mardi Santoso2
1School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2-B1-14, 637459, Singapore.
Abstract:
A simple trimethylsilyl trifluoromethanesulfonate (TMSOTf)-promoted intermolecular cascade reaction of aromatic diazo ketones with olefins has been developed. This method directly gave 3-phenylethylideneoxindoles from 3-diazooxindoles and styrenes with exclusive regioselectivity, chemoselectivity, and E-stereoselectivity. The key to the success of the reaction and higher yields is the elegant use of TMSOTf, which gradually released the active triflic acid promoter in situ. The reaction tolerates a wide substrate scope of 3-diazooxindoles and styrenes with electron-donating and electron-withdrawing groups and works well on the gram scale.
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