29328-21-0Relevant articles and documents
Iodine-promoted direct thiolation (selenylation) of imidazole with disulfides (diselenide): A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazole
Yi, Rongnan,Liu, Sen,Gao, Hongxia,Liang, Zhiwu,Xu, Xinhua,Li, Ningbo
, (2020)
A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazoles from imidazoles and disulfides (diselenides) was developed through the direct thiolation (selenylation) of imidazoles promoted by 0.5 equiv. of iodine. This process is
Meyer-Schuster-type rearrangement for the synthesis of α-selanyl-α,β-unsaturated thioesters
Baldassari, Lucas L.,Mantovani, Anderson C.,Jardim, Micaela,Maryasin, Boris,Lüdtke, Diogo S.
supporting information, p. 117 - 120 (2021/01/14)
A new approach to prepare α-selanyl-α,β-unsaturated thioesters from propargylthioalkynes and an electrophilic selenium species is reported. Pivotal is the intermediacy of a sulfur-stabilized vinyl cation, which is captured intramolecularly and ultimately
Iodine-catalyzed, highly atom-economic synthesis of 9-sulfenylphenanthrenes and polycyclic heteroaromatics in water
Mukherjee, Nilanjana,Chatterjee, Tanmay
, p. 10006 - 10013 (2021/12/24)
A highly atom-economical and green synthetic method is developed for the oxidative thiolative annulation of 2-alkynyl biaryls with disulfides to synthesize a wide variety of 9-sulfenylphenanthrenes and polycyclic heteroaromatics in water. The transformation requires only a couple of inexpensive reagents, i.e., iodine as a catalyst and hydrogen peroxide (H2O2) as a green oxidant, to furnish the desired products in good to excellent yield. The notable advantages of this protocol over the previously developed synthetic methods are a metal-free, cost-effective, and highly atom economic (>90%) protocol, use of inexpensive reagents as the catalyst and green oxidant, use of water as the reaction medium, very high (>95%) carbon efficiency (water as the major waste), broad substrate scope, high functional group tolerance, high yields of products up to 95%, straight-forward scale-up process upto 10 g scale and significantly, low E-factor (2.25) and high EcoScale score (67).
Regioselective deoxygenative chalcogenation of 7-Azindole: N-oxides promoted by I2/PEG-200
Liu, Shanshan,Yang, Heng,Jiao, Lin-Yu,Zhang, Jian-Hua,Zhao, Chen,Ma, Yangmin,Yang, Xiufang
supporting information, p. 10073 - 10087 (2019/12/23)
We developed a general and sustainable approach for the regioselective deoxygenative chalcogenation of 7-Azindole N-oxides; the combination of an internal oxidant and a green solvent has been used successfully for the synthesis of mono-and dichalcogenyl 7-Azaindoles which are of pharmaceutical interest. The regioselectivity is tunable by the variation of the reaction conditions. I2/PEG was established as an efficient and reusable catalytic system for C-H chalcogenation. This developed methodology has great potential for practical utility, with a broad substrate scope, green reaction conditions, and operational simplicity.
Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
supporting information, p. 2808 - 2811 (2016/07/06)
A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
Iron-facilitated iodine-mediated electrophilic annulation of N,N-dimethyl-2-alkynylanilines with disulfides or diselenides
Du, Hui-Ai,Tang, Ri-Yuan,Deng, Chen-Liang,Liu, Yan,Li, Jin-Heng,Zhang, Xing-Guo
scheme or table, p. 2739 - 2748 (2011/12/01)
An efficient synthesis of N-methyl-3-chalcogeno-indoles has been developed via iodine-mediated electrophilic annulation reactions of 2-alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2-alkynylani
