Unsymmetrical Aryl(2,4,6-trimethoxyphenyl) Iodonium Salts: One-Pot Synthesis, Scope, Stability, and Synthetic Studies
We acknowledge Portland State University and the donors of the American Chemical Society Petroleum Research Fund (PRF DNI1 #54405) for support of this research.
Journal of Organic Chemistry
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 (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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Seidl, T. L., Sundalam, S. K., McCullough, B., & Stuart, D. R. (2016). Unsymmetrical Aryl (2, 4, 6-trimethoxyphenyl) iodonium Salts: One-Pot Synthesis, Scope, Stability, and Synthetic Studies. The Journal of organic chemistry, 81(5), 1998-2009.