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Soft–Hard Acid–Base‐Controlled C−H Trifluoroethoxylation and Trideuteriomethoxylation of Anilides
Author(s) -
Maiti Saikat,
Alam Toufique,
Mal Prasenjit
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800069
Subject(s) - nucleophile , chemistry , electrophile , aryl , base (topology) , ion , carbenium ion , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , alkyl , mathematical analysis , mathematics
Phenyliodinetrifluoroacetate (PIFA)‐mediated dehydrogenative C−H etherification of anilides is reported for the synthesis of ‐OCH 2 CF 3 and ‐OCD 3 incorporated aryl ethers. Nucleophilicity of the added nucleophiles and soft–hard acid–base (SHAB) principle were rationalized to understand those reactions. Anilides and PIFA led to the electrophiles either softer nitrenium ions or harder carbenium ions. The harder nucleophile alcohols exclusively reacted with the carbenium ions to produce aryl ethers.