Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)-H arylation of 3-aminosugars

Juba Ghouilem; Sokna Bazzi; Nicolas Grimblat; Pascal Retailleau; Vincent Gandon; Samir Messaoudi

doi:10.1039/d3cc00046j

Transient imine as a directing group for the Pd-catalyzed anomeric C(sp³)-H arylation of 3-aminosugars

Juba Ghouilem
, Sokna Bazzi
, Nicolas Grimblat
, Pascal Retailleau
, Vincent Gandon
, Samir Messaoudi

Université Paris-Sud
CNRS
Institut de Chimie des Substances Naturelles
Institut de Chimie Moléculaire et des Matériaux d'Orsay

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

Résumé

The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

langue originale	Anglais
Pages (de - à)	2497-2500
Nombre de pages	4
journal	Chemical Communications
Volume	59
Numéro de publication	17
Les DOIs	https://doi.org/10.1039/d3cc00046j
état	Publié - 31 janv. 2023
Modification externe	Oui

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10.1039/d3cc00046j

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abstract = "The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.",

author = "Juba Ghouilem and Sokna Bazzi and Nicolas Grimblat and Pascal Retailleau and Vincent Gandon and Samir Messaoudi",

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doi = "10.1039/d3cc00046j",

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T1 - Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)-H arylation of 3-aminosugars

AU - Ghouilem, Juba

AU - Bazzi, Sokna

AU - Grimblat, Nicolas

AU - Retailleau, Pascal

AU - Gandon, Vincent

AU - Messaoudi, Samir

PY - 2023/1/31

Y1 - 2023/1/31

N2 - The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

AB - The first example of Pd(ii)-catalyzed anomeric arylation of 3-aminosugars is reported by using an L,X-type transient directing group (TDG) approach combined with an external 2-pyridone ligand. The released free amine was in situ transformed into an azide function, which was then exploited in a CuAAC to increase the molecular complexity and prepare a variety of complex substituted C3-triazolo C-glycosides in good yields.

U2 - 10.1039/d3cc00046j

DO - 10.1039/d3cc00046j

M3 - Article

C2 - 36752765

AN - SCOPUS:85148437732

SN - 1359-7345

VL - 59

SP - 2497

EP - 2500

JO - Chemical Communications

JF - Chemical Communications

IS - 17

ER -

Transient imine as a directing group for the Pd-catalyzed anomeric C(sp3)-H arylation of 3-aminosugars

Résumé

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Contient cette citation

Transient imine as a directing group for the Pd-catalyzed anomeric C(sp³)-H arylation of 3-aminosugars