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

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• 作者：Steven M. Langdon ; Myron M. D. Wilde ; Karen Thai ; Michel Gravel
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：May 28, 2014
• 年：2014
• 卷：136
• 期：21
• 页码：7539-7542
• 全文大小：251K
• 年卷期：v.136,no.21(May 28, 2014)
• ISSN：1520-5126

文摘

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%).