23019-08-1Relevant articles and documents
C-H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates
Sch?mberg, Fritz,Vilotijevic, Ivan,Wagner, Konrad,Zi, You
supporting information, (2020/05/05)
Benzothiazoles undergo regioselective C2-H functionalization with triphenylphosphine to form thiazol-2-yl-triphenylphosphonium salts, and these phosphonium salts react with a wide range of O- A nd N-centered nucleophiles to give the corresponding ethers, amines, and C-N biaryls. The reactions proceed under mild conditions and allow for the recovery of triphenylphosphine at the end of the sequence. In the presence of hydroxide, phosphonium salts undergo disproportionation, resulting in the reduction of the benzothiazole, which is useful for specific C2 deuteration of benzothiazoles.
Thieme Chemistry Journals Awardees - Where Are They Now? Rhodium-Catalyzed Synthesis of Unsymmetric Di(heteroaryl) Ethers Using Heteroaryl Exchange Reaction
Tanii, Saori,Arisawa, Mieko,Tougo, Takaya,Horiuchi, Kiyofumi,Yamaguchi, Masahiko
, p. 1601 - 1607 (2017/08/11)
Unsymmetric di(heteroaryl) ethers were synthesized by the rhodium-catalyzed heteroaryl exchange reaction of heteroaryl aryl ethers and heteroaryl esters at equilibrium. Diverse unsymmetric di(heteroaryl) ethers containing five- and six-membered heteroaren
The coupling reactions of aryl halides and phenols catalyzed by palladium and MOP-type ligands
Zhang, Yi,Ni, Gang,Li, Chengjun,Xu, Sheng,Zhang, Zhaoguo,Xie, Xiaomin
, p. 4927 - 4932 (2015/06/23)
Palladium-catalyzed coupling reactions of aryl halides and phenols are described employing the bulky and electron-rich MOP-type ligands. When K3PO4 was used as base and toluene as solvent, the catalyst system exhibited high efficiency for the coupling reaction of the activated aryl halides. When NaH was used as base and o-xylene as solvent, unactivated aryl halides can be used as substrates.
Copper(I)-catalyzed cascade synthesis of 2-substituted 1,3-benzothiazoles: Direct access to benzothiazolones
Murru, Siva,Mondal, Pravat,Yella, Ramesh,Patel, Bhisma K.
experimental part, p. 5406 - 5413 (2010/02/28)
An efficient cascade process for the preparation of 2-substituted 1,3-benzothiazoles directly from 2-haloaryl isothiocyanates and O or S nucleophiles by a Cu-catalyzed, intramolecular, C-S bond formation has been developed. This cascade method is viable f
(2-Pyridyl)acetone-promoted Cu-catalyzed O-arylation of phenols with aryl iodides, bromides, and chlorides
Zhang, Qi,Wang, Deping,Wang, Xianyang,Ding, Ke
supporting information; experimental part, p. 7187 - 7190 (2009/12/09)
(Chemical Equation Presented) Employing (2-pyridyl)acetone as a new supporting ligand, the copper-catalyzed coupling reactions of aryl chlorides, aryl bromides, and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. This reaction displays great functional groups compatibility and excellent reactive selectivity.
Effect of microwave heating on Ullmann-type heterocycle-aryl ether synthesis using chloro-heterocycles
D'Angelo, Noel D.,Peterson, Joseph J.,Booker, Shon K.,Fellows, Ingrid,Dominguez, Celia,Hungate, Randall,Reider, Paul J.,Kim, Tae-Seong
, p. 5045 - 5048 (2007/10/03)
Ullmann ether synthesis was conducted on a variety of chloro-heterocycles with different phenols using optimized conditions involving copper powder and cesium carbonate. On many substrates, microwave heating afforded higher yields in significantly shorter reaction times compared to conventional heating conditions. These findings provide a facile method for aryl ether synthesis from chloropyridines, chloroquinolines, and chlorobenzothiazoles.
