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

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	530-533
Nombre de pages	4
journal	Organic Letters
Volume	13
Numéro de publication	3
Les DOIs	https://doi.org/10.1021/ol1029589
Etat de la publication	Publié - 4 févr. 2011
Modification externe	Oui

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10.1021/ol1029589

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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.",

author = "{De Rycke}, Nicolas and Guillaume Berionni and Fran{\c c}ois Couty and Herbert Mayr and Regis Goumont and David, {Olivier R.P.}",

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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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DO - 10.1021/ol1029589

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AN - SCOPUS:79851487286

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VL - 13

SP - 530

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JO - Organic Letters

JF - Organic Letters

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Synthesis and reactivity of highly nucleophilic pyridines

Résumé

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