Chemoselective N‑Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions: Importance of the Fused Ring in Triazolium Salts

Morpholinone- and piperidinone-derived triazolium salts are shown to catalyze highly chemoselective cross-benzoin reactions between aliphatic and aromatic aldehydes. The reaction scope includes ortho-, meta-, and para-substituted benzaldehyde derivatives with a range of electron-donating and -withdr...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-05, Vol.136 (21), p.7539-7542
Main Authors: Langdon, Steven M, Wilde, Myron M. D, Thai, Karen, Gravel, Michel
Format: Article
Language:English
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Summary:Morpholinone- and piperidinone-derived triazolium salts are shown to catalyze highly chemoselective cross-benzoin reactions between aliphatic and aromatic aldehydes. The reaction scope includes ortho-, meta-, and para-substituted benzaldehyde derivatives with a range of electron-donating and -withdrawing groups as well as branched and unbranched aliphatic aldehydes. Catalytic loadings as low as 5 mol % give excellent yields in these reactions (up to 99%).
ISSN:0002-7863
1520-5126
DOI:10.1021/ja501772m