Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers. Issue 2 (26th November 2019)

• Record Type: Journal Article
• Authors: Gallagher, Rory T.; Basu, Souradeep; Stuart, David R.
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 2(2020)
• Page Start: 320
• Page End: 325
• Publication Date: 2019-11-26
• Subjects: C−O cross-coupling -- telescoping -- hypervalent iodine -- diaryliodonium -- diaryl ether; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201901187
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :