Unsymmetrical Aryl(2,4,6-trimethoxyphenyl)iodonium Salts: One-Pot Synthesis, Scope, Stability, and Synthetic Studies
Autor: | David R. Stuart, Brennen McCullough, Thomas L. Seidl, Sunil K. Sundalam |
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Rok vydání: | 2016 |
Předmět: |
Reaction conditions
Molecular Structure 010405 organic chemistry Aryl Organic Chemistry One-pot synthesis Benzenesulfonates Substrate (chemistry) 010402 general chemistry 01 natural sciences High yielding Catalysis 0104 chemical sciences Chlorobenzoates chemistry.chemical_compound Onium Compounds chemistry Metals Liquid crystal molecule Reagent Organic chemistry Organic synthesis Indicators and Reagents Salts |
Zdroj: | The Journal of organic chemistry. 81(5) |
ISSN: | 1520-6904 |
Popis: | 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. |
Databáze: | OpenAIRE |
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