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

SM Langdon, MMD Wilde, K Thai…

Index: Langdon, Steven M.; Wilde, Myron M.D.; Thai, Karen; Gravel, Michel Journal of the American Chemical Society, 2014 , vol. 136, # 21 p. 7539 - 7542

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Citation Number: 24

Abstract

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 ...