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Volumn 9, Issue 26, 2007, Pages 5541-5544

Scope of a novel three-component synthesis of highly functionalized pyridines

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PYRIDINE DERIVATIVE;

EID: 38349127957     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702468s     Document Type: Article
Times cited : (93)

References (49)
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    • This intermediate could be isolated and characterized for R = t-Bu (see ref 1).
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    • Whereas methoxyallene was generally used in large excess (3 equiv) only 1 equiv of allenes 6a-c was employed. This may explain the moderate yields.
    • Whereas methoxyallene was generally used in large excess (3 equiv) only 1 equiv of allenes 6a-c was employed. This may explain the moderate yields.
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    • The lower yield may be due to side reactions of the 2-alkyl side chain during the relatively harsh conditions of the condensation step.
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    • Unfortunately, cyanopyridines were not suitable substrates for the addition of lithiated alkoxyallenes. So far, only complex mixtures of compounds were isolated
    • Unfortunately, cyanopyridines were not suitable substrates for the addition of lithiated alkoxyallenes. So far, only complex mixtures of compounds were isolated.
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    • The unpolar pyridyl nonaflates are much easier to separate from byproducts. Furthermore, they are excellent precursors for the anticipated palladium-catalyzed coupling reactions. For examples of the reactions of alkenyl nonaflates, see: Högermeier, J.; Reissig, H.-U. Chem. Eur. J. 2007, 13, 2410-2420 and references cited in this publication.
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    • Several of the compounds prepared show interesting photophysical properties, which will have to be investigated in more detail.
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