4.7 Article

Unsymmetrical Aryl(2,4,6-trimethoxyphenyl)iodonium Salts: One-Pot Synthesis, Scope, Stability, and Synthetic Studies

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 5, Pages 1998-2009

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02833

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Funding

  1. Portland State University
  2. 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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