1174014-08-4Relevant academic research and scientific papers
Efficient synthesis of unsymmetrical heteroaryl thioethers and chalcogenides by alkali hydroxide-mediated SNAr reactions of heteroaryl halides and dichalcogenides
Ma, Xiantao,Liu, Quan,Jia, Xiaojuan,Su, Chenliang,Xu, Qing
, p. 56930 - 56935 (2016/07/06)
An efficient alkali hydroxide-mediated SNAr reaction of heteroaryl halides has been developed for the practical synthesis of the useful unsymmetrical heteroaryl thioethers and chalcogenides. The usually odorless, easily available, lowly toxic, and easily stored and handled diorganyl dichalcogenides can be used as safer and convenient chalcogen nucleophile precursors and diverse unsymmetrical heteroaryl chalcogenides can be obtained in good to high yields by the method.
Sulfur-silicon bond activation catalysed by Cl/Br ions: Waste-free synthesis of unsymmetrical thioethers by replacing fluoride catalysis and fluorinated substrates in SNAr reactions
Jia, Xiaojuan,Yu, Lei,Liu, Jianping,Xu, Qing,Sickert, Marcel,Chen, Lianhui,Lautens, Mark
supporting information, p. 3444 - 3449 (2014/07/08)
In contrast to conventional activation of Nu-SiR3 reagents by F ion attributed to the strong affinity of Si to F, S-Si activation can now be achieved using Cl/Br ions of TBAX as catalysts via formation of weaker X-Si bonds and Me3Si-X. This led to a waste-free synthesis of unsymmetrical thioethers via F-free SNAr reactions of activated (hetero)aryl halides and RS-SiMe3, with recovery of the useful Me3Si-X reagent in high yields. This journal is the Partner Organisations 2014.
Efficient copper(I)-catalyzed C-S cross-coupling of thiols with aryl halides in an aqueous two-phase system
Zhang, Xin-Yan,Zhang, Xiao-Yan,Guo, Sheng-Rong
experimental part, p. 23 - 35 (2011/12/05)
A mild and convenient C-S bond formation reaction catalyzed by CuI/L-proline in an aqueous two-phase system was achieved, providing a simple method for the synthesis of aryl sulfides in good yields.
Catalyst-free and base-free water-promoted SNAr reaction of heteroaryl halides with thiols
Sreedhar,Surendra Reddy,Amarnath Reddy
experimental part, p. 1732 - 1738 (2009/12/26)
A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products. Georg Thieme Verlag Stuttgart.
Green chemical synthesis of 2-benzenesulfonyl-pyridine and related derivatives
Trankle, William G.,Kopach, Michael E.
supporting information, p. 913 - 917 (2012/12/30)
A practical synthesis of 2-benzenesulfonylpyridine, 1, is described which is a key starting material for the manufacture of an investigational new drug candidate at Eli Lilly and Company. An optimized green chemical process was developed which features a novel tandem SNAr/oxidation under mild conditions to produce the target sulfone, 1, in 86% yield and>99% purity. In addition, this novel, environmentally friendly methodology was found to be general for the synthesis of substituted aromatic pyridyl sulfides and sulfones.
