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

Published In

Journal of Organic Chemistry

Document Type

Citation

Publication Date

2-1-2016

Abstract

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.

DOI

10.1021/acs.joc.5b02833

Persistent Identifier

http://archives.pdx.edu/ds/psu/18857

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