期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 53, 页码 13249-13258出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201703057
关键词
aryl ethers; arynes; hypervalent iodine; mechanistic study; oxidation
资金
- Swedish Research Council [621-2011-3608, 2015-04404]
- Swedish Research Council [2015-04404] Funding Source: Swedish Research Council
A mechanistic study of arylations of aliphatic alcohols and hydroxide with diaryliodonium salts, to give alkyl aryl ethers and diaryl ethers, has been performed using experimental techniques and DFT calculations. Aryne intermediates have been trapped, and additives to avoid by-product formation originating from arynes have been found. An alcohol oxidation pathway was observed in parallel to arylation; this is suggested to proceed by an intramolecular mechanism. Product formation pathways via ligand coupling and arynes have been compared, and 4-coordinated transition states were found to be favored in reactions with alcohols. Furthermore, a novel, direct nucleophilic substitution pathway has been identified in reactions with electron-deficient diaryliodonium salts.
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