| Aryl sulfides and derivatives are an important class of organic and pharmaceutical synthesis intermediates. Bcause of the important biological activity,they have been widely used in the fields of pesticides and medicine. So it has great significance for the synthesis of aryl sulfide compounds. In this thesis, synthesis and application of aryl sulfide compound were simply reviewed; and we develop an iodine-triphenylphosphine metal-free mediated C-H directly active C-S coupling reaction of 2-naphthols/2-naphthylamines/indoles by using simple and available sodium arylsulfinates as a sulfur source, achieving aryl thioethers in moderate to excellent yields in mild conditions.The results proved that a series of diaryl thioethers compounds were effectively obtained with a mixture of 2-naphthols/2-naphthylamines/indoles(0.3 mmol), sodium arylsulfinates(0.6 mmol), iodine(0.3 mmol)-triphenylphosphine(0.6 mmol) mediated,in diglyme(2 m L), 100 ℃ for 24 h under sealed condition(Scheme 1). In this transformation, a series of substituted sodium arylzenesulfinates smoothly reacted with 2-naphthols/2-naphthylamines/indoles to give aryl thioethers in good to high yields. Various 2-naphthol/indole derivatives for this kind of reaction were also tested in moderate to excellent yields. Seriously, the indole derivatives with strong electronwithdrawing groups on the phenyl rings for this transformation were also proceeded smoothly and afforded the corresponding products in good yields. The reaction has some advantages of metal-free, simple, efficient, mild, wide scope of substrates.Functional groups such as halogens and trifluoromethyl tolerated well under the optimized reaction conditions. The method represents a facile and metal-free way to access unsymmetrical di(hetero)aryl thioethers. |
