Arynes in a three-component coupling reaction: Straightforward synthesis of benzoannulated iminofurans

Angewandte Chemie - International Edition

Volumn 43, Issue 30, 2004, Pages 3935-3938

  Yoshida, Hiroto ^a   Fukushima, Hiroyuki ^a   Ohshita, Joji ^a   Kunai, Atsutaka ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Arynes; Isocyanides; Multicomponent reactions; Oxygen heterocycles; Regioselectivity

Indexed keywords

ALDEHYDES; FURAN RESINS; ISOMERS;

REGIOISOMERS; REGIOSELECTIVITY; THREE-COMPONENT COUPLING REACTION;

AROMATIC COMPOUNDS;

ALDEHYDE; BENZENE DERIVATIVE; CYANIDE; FURAN DERIVATIVE; IMINE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 4544320921     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460009     Document Type: Article

References (34)

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28. Owing to the complexity of the reaction mixtures, we did not pursue the identification of by-products of low-yielding reactions. At present, the reasons for which the desired products formed in low yields in the reactions of 1e, 1i, and 1j are unclear.
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30. A referee suggested another mechanism, in which the isocyanide acts as an electrophile: Nucleophilic attack of the oxygen atom of the carbonyl group of the aldehyde at the carbon atom of the isocyanide group produces a 1,3-dipole, which then undergoes 1,3-dipolar cycloaddition with an aryne to afford the product. Although this alternative mechanism can not be ruled out entirely, the mechanism proposed by us appears more likely, as the electrophilic coupling of an isocyanide with a neutral nucleophile is generally known to be sluggish, except in special cases. Furthermore, if the oxygen atom of the carbonyl group acted as a nucleophile, it would first interact with the highly electrophilic aryne, rather than the isocyanide, to provide a different product to those described herein. For the electrophilic coupling of an isocyanide with a neutral nucleophile, see: a) M. Suginome, T. Fukuda, Y. Ito, Org. Lett. 1999, 1, 1977;
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