Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions

Atul A. More; Sourav K. Santra; Alex M. Szpilman

doi:10.1021/acs.orglett.9b03824

Azido-Enolonium Species in C-C and C-N Bond-Forming Coupling Reactions

Atul A. More, Sourav K. Santra, Alex M. Szpilman

Department of Chemical Sciences

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	768-771
Number of pages	4
Journal	Organic Letters
Volume	22
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.9b03824
State	Published - 7 Feb 2020

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abstract = "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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AB - 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

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