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

Thomas L. Seidl, Sunil K. Sundalam, Brennen McCullough and David R. Stuart*

*Department of Chemistry, Portland State University, Portland, Oregon 97201, United States, Email: dstuartpdx.edu

T. L. Seidl, S. K. Sundalam, B. McCullough, D. R. Stuart, J. Org. Chem., 2016, 81, 1998-2009.

DOI: 10.1021/acs.joc.5b02833 (free Supporting Information)


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Abstract

A one-pot synthesis of aryl(2,4,6-trimethoxyphenyl)iodonium salts from aryl iodides, m-CPBA, p-toluenesulfonic acid, and trimethoxybenzene is fast, provides a high yield of product, and has broad substrate scope. The utility of these reagents is demonstrated in arylation reactions with C-, N-, O-, and S-nucleophiles.

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Synthesis of Aryl(2,4,6-trimethoxyphenyl)iodonium Trifluoroacetate Salts

V. Carreras, A. H. Sandtorv, D. R. Stuart, J. Org. Chem., 2017, 82, 1279-1284.


Key Words

iodonium salts, MCPBA


ID: J42-Y2016