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Cation‐π Assisted Synthesis of Alkyl Aryl Ethers via C‐CN Functionalization of 1,2‐Dicyano Pyrazines
Author(s) -
Achar Tapas Kumar,
Sahoo Prasit Kumar,
Mal Prasenjit
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700210
Subject(s) - chemistry , nucleophilic aromatic substitution , surface modification , aryl , alkyl , nucleophile , nucleophilic substitution , medicinal chemistry , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
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 n Bu 4 N + and aliphatic alcohols. We anticipated that weak interaction (soft force) like cation‐π was operative to activate the C‐CN bond for aromatic nucleophilic (S N Ar) ipso substitution. Thus demonstrated the weakening of strong chemical bonds could be done via collection of cooperative and weak interactions (soft fore relay).