<i>N</i>‐Acyliminium Ion Chemistry: Highly Efficient and Versatile Carbon–Carbon Bond Formation by Nucleophilic Substitution of Hydroxy Groups Catalyzed by Sn(NTf<sub>2</sub>)<sub>4</sub>

Raja Ben Othman, Radouane Affani, Marie‐José Tranchant, Sylvain Antoniotti, Vincent Dalla, Élisabet Duñach

Angewandte Chemie International Edition · 2009 · 72 citations · 71 references

Abstract

Atom-economical: Unmodified hemi-N,O-acetals are used in a catalytic, highly efficient α-amidoalkylation of a broad range of carbon-centered nucleophiles, including silicon-based components, active methylene derivatives, electron-rich arenes, and even simple ketones (see scheme). The reactions proceed in a highly efficient manner and typically require only 1 mol % of the Lewis superacidic reagent Sn(NTf2)4 as the catalyst. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

References

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