A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction

Davide Audisio; Samir Messaoudi; Jean François Peyrat; Jean Daniel Brion; Mouâd Alami

doi:10.1016/j.tetlet.2007.07.166

A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction

Davide Audisio, Samir Messaoudi, Jean François Peyrat, Jean Daniel Brion, Mouâd Alami

Université Paris-Saclay

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

Abstract

A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readily available 3-bromocoumarin derivatives in the presence of the catalytic system Pd(OAc)₂/Xantphos. Under these conditions, a series of nucleophiles including amides, sulfonamides, carbamates and functionalized amines, have been successfully reacted to afford the coupling products in fair to good yields.

Original language	English
Pages (from-to)	6928-6932
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.166
Publication status	Published - 24 Sept 2007
Externally published	Yes

Keywords

3-(N-substituted) aminocoumarins
3-Bromocoumarins
C-N bond coupling reaction
Palladium

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10.1016/j.tetlet.2007.07.166

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title = "A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction",

abstract = "A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readily available 3-bromocoumarin derivatives in the presence of the catalytic system Pd(OAc)2/Xantphos. Under these conditions, a series of nucleophiles including amides, sulfonamides, carbamates and functionalized amines, have been successfully reacted to afford the coupling products in fair to good yields.",

keywords = "3-(N-substituted) aminocoumarins, 3-Bromocoumarins, C-N bond coupling reaction, Palladium",

author = "Davide Audisio and Samir Messaoudi and Peyrat, \{Jean Fran{\c c}ois\} and Brion, \{Jean Daniel\} and Mou{\^a}d Alami",

year = "2007",

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doi = "10.1016/j.tetlet.2007.07.166",

language = "English",

volume = "48",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction

AU - Audisio, Davide

AU - Messaoudi, Samir

AU - Peyrat, Jean François

AU - Brion, Jean Daniel

AU - Alami, Mouâd

PY - 2007/9/24

Y1 - 2007/9/24

N2 - A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readily available 3-bromocoumarin derivatives in the presence of the catalytic system Pd(OAc)2/Xantphos. Under these conditions, a series of nucleophiles including amides, sulfonamides, carbamates and functionalized amines, have been successfully reacted to afford the coupling products in fair to good yields.

AB - A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readily available 3-bromocoumarin derivatives in the presence of the catalytic system Pd(OAc)2/Xantphos. Under these conditions, a series of nucleophiles including amides, sulfonamides, carbamates and functionalized amines, have been successfully reacted to afford the coupling products in fair to good yields.

KW - 3-(N-substituted) aminocoumarins

KW - 3-Bromocoumarins

KW - C-N bond coupling reaction

KW - Palladium

U2 - 10.1016/j.tetlet.2007.07.166

DO - 10.1016/j.tetlet.2007.07.166

M3 - Article

AN - SCOPUS:34548324619

SN - 0040-4039

VL - 48

SP - 6928

EP - 6932

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction

Abstract

Keywords

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