Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 5, Pages 1998-2009Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02833
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Funding
- Portland State University
- Biomolecular Mass Spectrometry Core of the Environmental Health Sciences Core Center at Oregon State University from National Institute of Environmental Health Science (NIEHS), National Institute of Health (NIH) [P30ES000210]
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Diaryliodonium salts have recently attracted significant attention as metal-free-arylation reagents in organic synthesis, and efficient access to these salts is critical for advancement of their use in reaction discovery and development. The trimethoxybenzene-derived auxiliary is a promising component of unsymmetrical variants, yet access remains limited. Here, a one-pot synthesis of aryl(2,4,6-trimethoxyphenyl)iodonium salts from aryl iodides, m-CPBA, p-toluenesulfonic acid, and trimethoxybenzene is described. Optimization of the reaction conditions for this one-pot synthesis was enabled by the method of multivariate analysis. The reaction is fast (<1 h), provides a high yield of product (>85% average), and has broad substrate scope (>25 examples) including elaborate aryl iodides. The utility of these reagents is demonstrated in moderate to high yielding arylation reactions with C-, N-, O-, and S-nucleophiles including the synthesis of a liquid crystal molecule.
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