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

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

Research output: Contribution to journalArticlepeer-review

17 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 languageEnglish
Pages (from-to)768-771
Number of pages4
JournalOrganic Letters
Volume22
Issue number3
DOIs
StatePublished - 7 Feb 2020

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