A site selective C-H arylation of free-(NH2) adenines with aryl chlorides: Application to the synthesis of 6,8-disubstituted adenines

Sophian Sahnoun; Samir Messaoudi; Jean Daniel Brion; Mouâd Alami

doi:10.1039/b912033e

A site selective C-H arylation of free-(NH₂) adenines with aryl chlorides: Application to the synthesis of 6,8-disubstituted adenines

Sophian Sahnoun
, Samir Messaoudi
, Jean Daniel Brion
, Mouâd Alami

Université Paris-Saclay

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

Abstract

An efficient site selective method for the direct arylation of free-(NH₂) adenines 1 to provide a range of C-8 arylated adenines 3 in excellent yields is described. This process based on the use of Pd(OH) ₂/C as the catalyst and a stoichiometric amount of CuI under ligandless conditions is general. It allows the coupling to proceed with a variety of aryl halides, including for the first time cheaper and less reactive aryl chlorides. The extension of this process for the sequential preparation of non-symmetrical C8/N⁶-arylated adenines 4 is also reported.

Original language	English
Pages (from-to)	4271-4278
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	7
Issue number	20
DOIs	https://doi.org/10.1039/b912033e
Publication status	Published - 1 Jan 2009
Externally published	Yes

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10.1039/b912033e

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abstract = "An efficient site selective method for the direct arylation of free-(NH2) adenines 1 to provide a range of C-8 arylated adenines 3 in excellent yields is described. This process based on the use of Pd(OH) 2/C as the catalyst and a stoichiometric amount of CuI under ligandless conditions is general. It allows the coupling to proceed with a variety of aryl halides, including for the first time cheaper and less reactive aryl chlorides. The extension of this process for the sequential preparation of non-symmetrical C8/N6-arylated adenines 4 is also reported.",

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T2 - Application to the synthesis of 6,8-disubstituted adenines

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AU - Brion, Jean Daniel

AU - Alami, Mouâd

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AB - An efficient site selective method for the direct arylation of free-(NH2) adenines 1 to provide a range of C-8 arylated adenines 3 in excellent yields is described. This process based on the use of Pd(OH) 2/C as the catalyst and a stoichiometric amount of CuI under ligandless conditions is general. It allows the coupling to proceed with a variety of aryl halides, including for the first time cheaper and less reactive aryl chlorides. The extension of this process for the sequential preparation of non-symmetrical C8/N6-arylated adenines 4 is also reported.

U2 - 10.1039/b912033e

DO - 10.1039/b912033e

M3 - Article

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 20

ER -

A site selective C-H arylation of free-(NH2) adenines with aryl chlorides: Application to the synthesis of 6,8-disubstituted adenines

Abstract

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A site selective C-H arylation of free-(NH₂) adenines with aryl chlorides: Application to the synthesis of 6,8-disubstituted adenines