Cation‐π Assisted Synthesis of Alkyl Aryl Ethers via C‐CN Functionalization of 1,2‐Dicyano Pyrazines

In 1,2‐dicyano pyrazines, functionalization of C‐CN to C‐O bond yielded alkyl aryl ethers quantitatively within 10 minutes at room temperature using cations nBu4N+ and aliphatic alcohols. We anticipated that weak interaction (soft force) like cation‐π was operative to activate the C‐CN bond for arom...

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Published in:ChemistrySelect (Weinheim) 2017-02, Vol.2 (5), p.1944-1949
Main Authors: Achar, Tapas Kumar, Sahoo, Prasit Kumar, Mal, Prasenjit
Format: Article
Language:English
Subjects:
Anion-π
Aryl alkyl ethers
C-CN activation
Cation-π
Transition metal free synthesis
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description In 1,2‐dicyano pyrazines, functionalization of C‐CN to C‐O bond yielded alkyl aryl ethers quantitatively within 10 minutes at room temperature using cations nBu4N+ and aliphatic alcohols. We anticipated that weak interaction (soft force) like cation‐π was operative to activate the C‐CN bond for aromatic nucleophilic (SNAr) ipso substitution. Thus demonstrated the weakening of strong chemical bonds could be done via collection of cooperative and weak interactions (soft fore relay). Towards weakening of strong chemical bonds via soft fore relay is important to make new chemical systems with functions. The soft force like cation‐π was operative in activation of C‐CN bond for aromatic nucleophilic (SNAr) ipso substitution under metal free condition. In 1,2‐dicyanopyrazines functionalization of C‐CN to C‐O bond resulted in alkyl aryl ethers using the combination of cations nBu4N+ or Na+, aliphatic alcohols and respective pyrazine derivatives.
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subjects Anion-π
Aryl alkyl ethers
C-CN activation
Cation-π
Transition metal free synthesis
title Cation‐π Assisted Synthesis of Alkyl Aryl Ethers via C‐CN Functionalization of 1,2‐Dicyano Pyrazines
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