14204-24-1Relevant articles and documents
Lewis Base/Bronsted Acid Dual-Catalytic C-H Sulfenylation of Aromatics
Nalbandian, Christopher J.,Brown, Zachary E.,Alvarez, Erik,Gustafson, Jeffrey L.
, p. 3211 - 3214 (2018)
A Lewis base/Bronsted acid catalyzed aromatic sulfenylation is reported. These studies demonstrated that the incorporation of electron-rich sulfenyl groups proceeded in the absence of a Lewis base, with kinetic studies indicating an autocatalytic mechanism. The incorporation of electron-poor sulfenyl groups demonstrated little autocatalysis necessitating the use of a Lewis base. This method proved amenable to diverse arenes and heterocycles and was effective in the context of the late-stage functionalization of biologically active small molecules.
Catalytic enantioselective oxysulfenylation ofo-vinylanilides
Anbarasan, Pazhamalai,Kesavan, Arunachalam
supporting information, p. 282 - 285 (2022/01/06)
Tf2NH-assisted BINAM-derived thiophosphoramide catalysis has been accomplished for the enantioselective oxysulfenylation ofo-vinylanilides withN-(aryl/alkylthio)imides. The developed reaction offers access to diverse substituted aryl/alkylthio
Regioselective C-H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis
Dodds, Amy C.,Sutherland, Andrew
, p. 5922 - 5932 (2021/05/04)
A mild and regioselective method for the preparation of unsymmetrical biaryl sulfides using iron(III) catalysis is described. Activation of N-(arylthio)succinimides using the powerful Lewis acid iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine. Kinetic studies revealed that while N-(arylthio)succinimides bearing electron-deficient arenes underwent thioarylation catalyzed entirely by iron(III) triflimide, N-(arylthio)succinimides with electron-rich arenes displayed an autocatalytic mechanism promoted by the Lewis basic product.
3-Thiolated pyrroles/pyrrolines: controllable synthesis and usage for the construction of thiolated fluorophores
Tian, Jun,Yuan, Kang-Ning,Liu, Wen,Chang, Hong-Hong,Li, Xing,Gao, Wen-Chao
supporting information, p. 1943 - 1946 (2021/03/02)
Thiolation/cyclization of homopropargylic tosylamides allowed the selective synthesis of 3-thiolated pyrroles and pyrrolines controlled by solvents. Moreover, the desired 3-thiolated pyrroles were readily transformed to organic fluorophores benzothienopyrrole and bisthiolated boron dipyrromethene (S-BODIPY).
