Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown azido-enolonium species react efficiently with aromatic compounds, allyltrimethylsilane, and azoles under mild conditions, with no need for a transition-metal catalyst, forming C-C and C-N bonds to give a variety of α-functionalized ketones. The intermediacy of the proposed azido-enolonium species is supported by spectroscopic studies.
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Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions.
Org Lett
February 2020
Department of Chemical Sciences, Faculty of Natural Sciences , Ariel University, Ariel 4070000 , Israel.
Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown azido-enolonium species react efficiently with aromatic compounds, allyltrimethylsilane, and azoles under mild conditions, with no need for a transition-metal catalyst, forming C-C and C-N bonds to give a variety of α-functionalized ketones. The intermediacy of the proposed azido-enolonium species is supported by spectroscopic studies.
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