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 inJournal of the American Chemical Society Vol. 136; no. 21; pp. 7539 - 7542
Main Authors Langdon, Steven M, Wilde, Myron M. D, Thai, Karen, Gravel, Michel
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.05.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
ACYLOIN CONDENSATIONS
MECHANISM
AZOLIUMS
STETTER REACTION
AROMATIC-ALDEHYDES
CARBOLIGATION
BICYCLIC THIAZOLIUM SALTS
ALIPHATIC-ALDEHYDES
SELECTIVITY
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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