Abstract:A series of well-defined copper(I) fluoroalkoxide complexes, [(phen) 2 Cu][OCH 2 R F ], have been shown to undergo trifluoroethoxylation, pentafluoropropoxylation, and tetrafluoropropoxylation with aryl and heteroaryl bromides to generate the corresponding trifluoroethyl, pentafluoropropyl, and tetrafluoropropyl (hetero)aryl ethers in good to excellent yields. The reaction tolerates a variety of functional groups and demonstrates efficient scalability and practicality.
Phenyliodinetrifluoroacetate (PIFA)-mediated dehydrogenative CÀHe therification 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 understandt hose reactions. Anilides and PIFAl ed 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.
Phenyliodinetrifluoroacetate (PIFA)-mediated dehydrogenative CÀHe therification 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 understandt hose reactions. Anilides and PIFAl ed 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.
The copper(I)‐mediated reaction delivers trifluoroethyl, pentafluoropropyl‐, and tetrafluoropropylaryl‐, and a broad range of hetarylethers in generally high yields.
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