Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization

Ana Sofia Santos; M. Margarida Martins; Ana C. Mortinho; Artur M. S. Silva; M. Manuel B. Marques

doi:10.1016/j.tetlet.2020.152303

Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization

Ana Sofia Santos, M. Margarida Martins, Ana C. Mortinho, Artur M. S. Silva, M. Manuel B. Marques

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

5 Citations (Scopus)

Abstract

Aminopyridines are key building blocks for the synthesis of bioactive N-heterocyclic compounds such as azaindoles and imidazopyridines. However, the functionalization of aminopyridines is challenging, due to their electronic properties and coordination with metals. Herein we describe a reactivity study of aminopyridines under palladium-catalyzed reaction conditions. Several aminopyridines underwent a one-pot Pd-catalyzed C–N cross coupling reaction/C–H functionalization sequence affording azaindoles. The role of additives, ligands, and bases was investigated. This work consists of a platform for future studies on aminopyridines involving metal-catalyzed reactions and represents the first report on the direct conversion of non-halogenated aminopyridines into azaindoles via Pd-catalyzed C–H functionalization reactions.

Original language	English
Article number	152303
Journal	Tetrahedron Letters
Volume	61
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2020.152303
Publication status	Published - 10 Sept 2020

Keywords

Aminopyridines
Azaindoles
Cross-coupling
C–H functionalization
Pd catalysis

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10.1016/j.tetlet.2020.152303

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title = "Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization",

abstract = "Aminopyridines are key building blocks for the synthesis of bioactive N-heterocyclic compounds such as azaindoles and imidazopyridines. However, the functionalization of aminopyridines is challenging, due to their electronic properties and coordination with metals. Herein we describe a reactivity study of aminopyridines under palladium-catalyzed reaction conditions. Several aminopyridines underwent a one-pot Pd-catalyzed C–N cross coupling reaction/C–H functionalization sequence affording azaindoles. The role of additives, ligands, and bases was investigated. This work consists of a platform for future studies on aminopyridines involving metal-catalyzed reactions and represents the first report on the direct conversion of non-halogenated aminopyridines into azaindoles via Pd-catalyzed C–H functionalization reactions.",

keywords = "Aminopyridines, Azaindoles, Cross-coupling, C–H functionalization, Pd catalysis",

author = "Santos, {Ana Sofia} and Martins, {M. Margarida} and Mortinho, {Ana C.} and Silva, {Artur M. S.} and Marques, {M. Manuel B.}",

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AU - Santos, Ana Sofia

AU - Martins, M. Margarida

AU - Mortinho, Ana C.

AU - Silva, Artur M. S.

AU - Marques, M. Manuel B.

N1 - UID/QUI/50006/2019 POCI-01-0145-FEDER – 007265 ROTEIRO/0031/2013 – PINFRA/22161/2016 PD/BD/142876/2018 Sem PDF conforme despacho.

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N2 - Aminopyridines are key building blocks for the synthesis of bioactive N-heterocyclic compounds such as azaindoles and imidazopyridines. However, the functionalization of aminopyridines is challenging, due to their electronic properties and coordination with metals. Herein we describe a reactivity study of aminopyridines under palladium-catalyzed reaction conditions. Several aminopyridines underwent a one-pot Pd-catalyzed C–N cross coupling reaction/C–H functionalization sequence affording azaindoles. The role of additives, ligands, and bases was investigated. This work consists of a platform for future studies on aminopyridines involving metal-catalyzed reactions and represents the first report on the direct conversion of non-halogenated aminopyridines into azaindoles via Pd-catalyzed C–H functionalization reactions.

AB - Aminopyridines are key building blocks for the synthesis of bioactive N-heterocyclic compounds such as azaindoles and imidazopyridines. However, the functionalization of aminopyridines is challenging, due to their electronic properties and coordination with metals. Herein we describe a reactivity study of aminopyridines under palladium-catalyzed reaction conditions. Several aminopyridines underwent a one-pot Pd-catalyzed C–N cross coupling reaction/C–H functionalization sequence affording azaindoles. The role of additives, ligands, and bases was investigated. This work consists of a platform for future studies on aminopyridines involving metal-catalyzed reactions and represents the first report on the direct conversion of non-halogenated aminopyridines into azaindoles via Pd-catalyzed C–H functionalization reactions.

KW - Aminopyridines

KW - Azaindoles

KW - Cross-coupling

KW - C–H functionalization

KW - Pd catalysis

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DO - 10.1016/j.tetlet.2020.152303

M3 - Article

AN - SCOPUS:85089253074

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

M1 - 152303

ER -

Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization

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Keywords

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