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Synfacts 2010(3): 0352-0352  
DOI: 10.1055/s-0029-1219409
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

NHC-Catalyzed Intramolecular Cross-Coupling of Aldehydes and Nitriles

Contributor(s): Benjamin List, Steffen Müller
S. Vedachalam, J. Zeng, B. Kishan Gorityala, M. Antonio, X.-W. Liu*
Nanyang Technological University, Singapore
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

The authors report the NHC-catalyzed intramolecular coupling between an aldehyde and a nitrile functionality. Treatment of precatalyst 1 with DBU gave the active NHC, which promoted the intramolecular ring-closure of differently substituted salicylic aldehyde derivatives very efficiently to give the corresponding 3-aminochromones in good to high yields. The proposed mechanism is supposed to be in analogy to the intramolecular benzoin condensation.