Synthesis and reactivity of highly nucleophilic pyridines

Nicolas De Rycke; Guillaume Berionni; François Couty; Herbert Mayr; Regis Goumont; Olivier R.P. David

doi:10.1021/ol1029589

Synthesis and reactivity of highly nucleophilic pyridines

Nicolas De Rycke, Guillaume Berionni, François Couty, Herbert Mayr, Regis Goumont, Olivier R.P. David

Research output: Contribution to journal › Article › peer-review

Abstract

3,4,5-Triamino-substituted pyridines are avid for electrophiles but are still willing to give them back. In these compounds three amino groups conjoin their forces into the heterocyclic nitrogen, making it a powerful Lewis base. A short and efficient synthesis is described, and the origin of its unique activity in nucleophilic organocatalysis is rationalized by kinetics and thermodynamic quantifications.

Original language	English
Pages (from-to)	530-533
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	3
DOIs	https://doi.org/10.1021/ol1029589
Publication status	Published - 4 Feb 2011
Externally published	Yes

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title = "Synthesis and reactivity of highly nucleophilic pyridines",

abstract = "3,4,5-Triamino-substituted pyridines are avid for electrophiles but are still willing to give them back. In these compounds three amino groups conjoin their forces into the heterocyclic nitrogen, making it a powerful Lewis base. A short and efficient synthesis is described, and the origin of its unique activity in nucleophilic organocatalysis is rationalized by kinetics and thermodynamic quantifications.",

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AU - De Rycke, Nicolas

AU - Berionni, Guillaume

AU - Couty, François

AU - Mayr, Herbert

AU - Goumont, Regis

AU - David, Olivier R.P.

PY - 2011/2/4

Y1 - 2011/2/4

N2 - 3,4,5-Triamino-substituted pyridines are avid for electrophiles but are still willing to give them back. In these compounds three amino groups conjoin their forces into the heterocyclic nitrogen, making it a powerful Lewis base. A short and efficient synthesis is described, and the origin of its unique activity in nucleophilic organocatalysis is rationalized by kinetics and thermodynamic quantifications.

AB - 3,4,5-Triamino-substituted pyridines are avid for electrophiles but are still willing to give them back. In these compounds three amino groups conjoin their forces into the heterocyclic nitrogen, making it a powerful Lewis base. A short and efficient synthesis is described, and the origin of its unique activity in nucleophilic organocatalysis is rationalized by kinetics and thermodynamic quantifications.

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JO - Organic Letters

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Synthesis and reactivity of highly nucleophilic pyridines

Abstract

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