150810-52-9Relevant academic research and scientific papers
NH4I/1,10-phenanthroline catalyzed direct sulfenylation of N-heteroarenes with ethyl arylsulfinates
Chen, Lingjuan,Zhang, Jun,Wei, Yueting,Yang, Zhen,Liu, Ping,Zhang, Jie,Dai, Bin
, (2019/10/14)
An efficient synthesis of N-heterocyclic aryl sulfides via NH4I/1,10-phenanthroline-catalyzed direct sulfenylation reactions was reported. In this reaction, heteroarenes such as indoles, and pyrroles serve as nucleophiles by installing a arylthio group at the C3 and C2 position of heterocycles, respectively. With readily accessible and free of unpleasant odor ethyl arylsulfinates as sulfur reagents, the metal-free-catalyzed direct sulfenylation of N-heteroarenes has been developed. 3-Arylthio-indoles and 2-arylthio-pyrroles derivatives were obtained in moderate to excellent yields, even on gram scale. The reaction was general for a broad scope of substrates and demonstrated good tolerance to a variety of functional groups.
Comparison of benzene, nitrobenzene, and dinitrobenzene 2-arylsulfenylpyrroles
Garabatos-Perera, Jose R.,Rotstein, Benjamin H.,Thompson, Alison
, p. 7382 - 7385 (2008/02/11)
(Chemical Equation Presented) The effectiveness of the 2,4- dinitrobenzenesulfenyl and 4-nitrobenzenesulfenyl groups as masking and directing groups at the 2-position of pyrrole has been investigated and compared to that of 2-phenylthiopyrrole. The presen
Sulfur-based protecting groups for pyrroles and the facile deprotection of 2-(2,4-dinitrobenzene)sulfinyl and sulfonyl pyrroles
Thompson, Alison,Butler, R. Jonathan,Grundy, Meaghan N.,Laltoo, Andrea B. E.,Robertson, Katherine N.,Cameron, T. Stanley
, p. 3753 - 3756 (2007/10/03)
(Chemical Equation Presented) The effectiveness of simple sulfinyl and sulfonyl groups as electron-withdrawing protecting groups for pyrroles has been analyzed using 13C NMR spectroscopy and confirmed by consideration of X-ray crystal structures. Additionally, the 2,4-dinitrobenzenesulfinyl and sulfonyl groups are shown to be effective electron-withdrawing protecting groups for pyrroles, and they can be removed by treatment with benzene thiol or thiolate under mild and specific conditions.
