Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers
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Advanced Synthesis & Catalysis
Herein, we describe a synthetic approach for arylation that exploits the in situ formation and reaction of an unsymmetrical diaryliodonium salt. In this way, aryl iodides are used as reagents in a metal‐free reaction with phenols, and a trimethoxyphenyl (TMP) group is used as a “dummy” group to facilitate transfer of a wide range of aryl moieties. The scope of aryl electrophiles and phenol nucleophiles is broad (>30 examples) and the yields are high (52–95%, 80% avg.). One‐pot coupling reactions avoid the synthesis of diaryliodonium salts and provide opportunities for sequential reactions and novel chemoselectivity.
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Gallagher, R., Basu, S., & Stuart, D. R. (2019). Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl (TMP) iodonium Salts: Synthesis of Diaryl Ethers. Advanced Synthesis & Catalysis.