98055-12-0Relevant academic research and scientific papers
Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation
Xiang, Haonan,Liu, Jie,Wang, Jieping,Jiang, Lvqi,Yi, Wenbin
supporting information, p. 181 - 185 (2021/12/17)
A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barr
Visible-light promoted synthesis of 3-arylthioindoles from indoles and diaryl disulfides
Ye, Lin-miao,Chen, Jie,Mao, Peng,Zhang, Xue-jing,Yan, Ming
supporting information, p. 2743 - 2746 (2017/06/23)
3-Arylthioindoles could be synthesized in good yields via the photoirradiation of indoles and disulfides. The reaction is efficiently promoted by the catalytic amount of sodium iodide. A reaction mechanism involving the electrophilic substitution of indol
Palladium-Catalyzed Oxidative Sulfenylation of Indoles and Related Electron-Rich Heteroarenes with Aryl Boronic Acids and Elemental Sulfur
Li, Jianxiao,Li, Chunsheng,Yang, Shaorong,An, Yanni,Wu, Wanqing,Jiang, Huanfeng
, p. 7771 - 7783 (2016/09/12)
An efficient and convenient palladium-catalyzed C-H bond oxidative sulfenylation of indoles and related electron-rich heteroarenes with aryl boronic acids and elemental sulfur has been described. This procedure provides a useful and direct approach for the assembly of a wide range of structurally diverse 3-sulfenylheteroarenes with moderate to excellent yields from simple and readily available starting materials. Moreover, this synthetic protocol is suitable for N-protected and unprotected indoles. Notably, the construction of two C-S bonds in one step was also achieved in this transformation.
Development of a novel, highly efficient halide-catalyzed sulfenylation of indoles
Tudge, Matthew,Tamiya, Minoru,Savarin, Cecile,Humphrey, Guy R.
, p. 565 - 568 (2007/10/03)
The reaction of a variety of indoles with N-thioalkyl- and N-thioarylphthalimides to produce 3-thioindoles is reported. Catalytic quantities of halide-containing salts are crucial to the success of this reaction. This highly efficient reaction provides sulfenylated indoles from bench-stable, readily available starting materials in good to excellent yields.
Facile and efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
Matsugi,Murata,Gotanda,Nambu,Anilkumar,Matsumoto,Kita
, p. 2434 - 2441 (2007/10/03)
A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.
A novel efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
Matsugi, Masato,Gotanda, Kentoku,Murata, Kenji,Kita, Yasuyuki
, p. 1387 - 1388 (2007/10/03)
A novel method for sulfenylation induced by aromatization of quinone mono-O,S-acetals is described.
Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides
Hamel, Pierre,Zajac, Nicolas,Atkinson, Joseph G.,Girard, Yves
, p. 6372 - 6377 (2007/10/02)
Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction.We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring.In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched.Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides.This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.
