2689-07-8Relevant articles and documents
Trimethoxyphenyl (TMP) as a Useful Auxiliary for in situ Formation and Reaction of Aryl(TMP)iodonium Salts: Synthesis of Diaryl Ethers
Gallagher, Rory T.,Basu, Souradeep,Stuart, David R.
, p. 320 - 325 (2019/12/11)
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. (Figure presented.).
Photocatalytic activation of N-chloro compounds for the chlorination of arenes
Hering, Thea,K?nig, Burkhard
, p. 7821 - 7825 (2016/11/16)
Photoredox catalysis activates N-chloramines and N-chloro-succinimide (NCS) for the electrophilic chlorination of arenes. The photooxidation of the nitrogen atom to a radical cation induces a positive polarization on the chlorine atom, which results in a higher reactivity in electrophilic aromatic chlorination reactions.
Copper-mediated synthesis of mono- and dichlorinated diaryl ethers
?ermák, Jan K.,Církva, Vladimír
supporting information, p. 4185 - 4188 (2014/07/22)
An efficient synthesis of polychlorinated diphenyl ethers (PCDEs) using the Cu(OAc)2-catalyzed Chan-Lam coupling reaction is described. A library of all possible mono- and dichlorinated diphenyl ether congeners was prepared and characterized using MS, 1H, and 13C NMR spectroscopy, and Kovats retention indices. Our approach, using the optimized reaction conditions (i.e., reaction temperature, oxidizing atmosphere and base), significantly improves and simplifies the process compared to previously reported syntheses.
