Microwave-assisted Pd(OH)2-catalyzed direct C-H arylation of free-(NH2) adenines with aryl halides

Sophian Sahnoun; Samir Messaoudi; Jean François Peyrat; Jean Daniel Brion; Mouad Alami

doi:10.1016/j.tetlet.2008.10.021

Microwave-assisted Pd(OH)₂-catalyzed direct C-H arylation of free-(NH₂) adenines with aryl halides

Sophian Sahnoun
, Samir Messaoudi
, Jean François Peyrat
, Jean Daniel Brion
, Mouad Alami

Université Paris-Saclay

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

Abstract

A direct C-H arylation of free-(NH₂) adenines using Pd(OH)₂/C (Pearlman's catalyst) and stoichiometric amount of copper iodide under ligandless microwave activation is described. This new protocol proved to be highly effective to synthesize a variety of 8-aryladenine derivatives 3 without prior protection of the amino substituent. The arylation reaction takes place rapidly within few minutes and allows the coupling to proceed regioselectively at the 8-position with a wide range of aryl halides including aryl iodides, bromides and the less reactive aryl chlorides.

Original language	English
Pages (from-to)	7279-7283
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2008.10.021
Publication status	Published - 15 Dec 2008
Externally published	Yes

Keywords

Adenines
Aryl chlorides
C-H arylation
Copper
Microwave irradiation
Palladium

Access to Document

10.1016/j.tetlet.2008.10.021

Cite this

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title = "Microwave-assisted Pd(OH)2-catalyzed direct C-H arylation of free-(NH2) adenines with aryl halides",

abstract = "A direct C-H arylation of free-(NH2) adenines using Pd(OH)2/C (Pearlman's catalyst) and stoichiometric amount of copper iodide under ligandless microwave activation is described. This new protocol proved to be highly effective to synthesize a variety of 8-aryladenine derivatives 3 without prior protection of the amino substituent. The arylation reaction takes place rapidly within few minutes and allows the coupling to proceed regioselectively at the 8-position with a wide range of aryl halides including aryl iodides, bromides and the less reactive aryl chlorides.",

keywords = "Adenines, Aryl chlorides, C-H arylation, Copper, Microwave irradiation, Palladium",

author = "Sophian Sahnoun and Samir Messaoudi and Peyrat, \{Jean Fran{\c c}ois\} and Brion, \{Jean Daniel\} and Mouad Alami",

year = "2008",

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day = "15",

doi = "10.1016/j.tetlet.2008.10.021",

language = "English",

volume = "49",

pages = "7279--7283",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Microwave-assisted Pd(OH)2-catalyzed direct C-H arylation of free-(NH2) adenines with aryl halides

AU - Sahnoun, Sophian

AU - Messaoudi, Samir

AU - Peyrat, Jean François

AU - Brion, Jean Daniel

AU - Alami, Mouad

PY - 2008/12/15

Y1 - 2008/12/15

N2 - A direct C-H arylation of free-(NH2) adenines using Pd(OH)2/C (Pearlman's catalyst) and stoichiometric amount of copper iodide under ligandless microwave activation is described. This new protocol proved to be highly effective to synthesize a variety of 8-aryladenine derivatives 3 without prior protection of the amino substituent. The arylation reaction takes place rapidly within few minutes and allows the coupling to proceed regioselectively at the 8-position with a wide range of aryl halides including aryl iodides, bromides and the less reactive aryl chlorides.

AB - A direct C-H arylation of free-(NH2) adenines using Pd(OH)2/C (Pearlman's catalyst) and stoichiometric amount of copper iodide under ligandless microwave activation is described. This new protocol proved to be highly effective to synthesize a variety of 8-aryladenine derivatives 3 without prior protection of the amino substituent. The arylation reaction takes place rapidly within few minutes and allows the coupling to proceed regioselectively at the 8-position with a wide range of aryl halides including aryl iodides, bromides and the less reactive aryl chlorides.

KW - Adenines

KW - Aryl chlorides

KW - C-H arylation

KW - Copper

KW - Microwave irradiation

KW - Palladium

U2 - 10.1016/j.tetlet.2008.10.021

DO - 10.1016/j.tetlet.2008.10.021

M3 - Article

AN - SCOPUS:55249095019

SN - 0040-4039

VL - 49

SP - 7279

EP - 7283

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51