126165-45-5Relevant articles and documents
Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids
Tripathy, Alisha Rani,Yatham, Veera Reddy,Yedase, Girish Suresh
, p. 25207 - 25210 (2021/08/05)
We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl3as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.
N-Heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement: Synthesis of aryl salicylates from: O -aryl salicylaldehydes
Xia, Zi-Hao,Dai, Lei,Gao, Zhong-Hua,Ye, Song
supporting information, p. 1525 - 1528 (2020/02/13)
The N-heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement of O-aryl salicylaldehydes was developed. Both electron-deficient and electron-rich aryls worked well as migrating groups, giving the corresponding aryl salicylates in good yields. This reaction features formation of two new C-O bonds and one C-O bond cleavage via metal-free oxidation of the Breslow intermediate using oxygen as the terminal oxidant and following the Smiles rearrangement under photocatalysis.
A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids
Gonzalez-Gomez, Jose C.,Ramirez, Nieves P.,Lana-Villarreal, Teresa,Bonete, Pedro
supporting information, p. 9680 - 9684 (2017/11/30)
We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.
Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement
Hossian, Asik,Jana, Ranjan
, p. 9768 - 9779 (2016/10/31)
We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.