557780-43-5Relevant academic research and scientific papers
Guest-controlled incommensurate modulation in a meta-rigid metal-organic framework material
Li, Jiangnan,Zhou, Zhengyang,Han, Xue,Zhang, Xinran,Yan, Yong,Li, Weiyao,Smith, Gemma L.,Cheng, Yongqiang,McCormick McPherson, Laura J.,Teat, Simon J.,Frogley, Mark D.,Rudi?, Svemir,Ramirez-Cuesta, Anibal J.,Blake, Alexander J.,Sun, Junliang,Schr?der, Martin,Yang, Sihai
, p. 19189 - 19197 (2020)
Structural transitions of host systems in response to guest binding dominate many chemical processes. We report an unprecedented type of structural flexibility within a meta-rigid material, MFM-520, which exhibits a reversible periodic-to-aperiodic structural transition resulting from a drastic distortion of a [ZnO4N] node controlled by the specific host-guest interactions. The aperiodic crystal structure of MFM-520 has no three-dimensional (3D) lattice periodicity but shows translational symmetry in higher-dimensional (3 + 2)D space. We have directly visualized the aperiodic state which is induced by incommensurate modulation of the periodic framework of MFM-520·H2O upon dehydration to give MFM-520. Filling MFM-520 with CO2 and SO2 reveals that, while CO2 has a minimal structural influence, SO2 can further modulate the structure incommensurately. MFM-520 shows exceptional selectivity for SO2 under flue-gas desulfurization conditions, and the facile release of captured SO2 from MFM-520 enabled the conversion to valuable sulfonamide products. MFM-520 can thus be used as a highly efficient capture and delivery system for SO2.
Design and Applications of a SO2 Surrogate in Palladium-Catalyzed Direct Aminosulfonylation between Aryl Iodides and Amines
Jia, Xiuwen,Kramer, S?ren,Skrydstrup, Troels,Lian, Zhong
supporting information, p. 7353 - 7359 (2021/02/26)
A new SO2 surrogate is reported that is cheap, bench-stable, and can be accessed in just two steps from bulk chemicals. Essentially complete SO2 release is achieved in 5 minutes. Eight established sulfonylation reactions proceeded smoothly by ex situ formation of SO2 by utilizing a two-chamber system in combination with the SO2 surrogate. Furthermore, we report the first direct aminosulfonylation between aryl iodides and amines. Broad functional group tolerance is demonstrated, and the method is applicable to pharmaceutically relevant substrates, including heterocyclic substrates.
Visible-Light Photoredox-Catalyzed Aminosulfonylation of Diaryliodonium Salts with Sulfur Dioxide and Hydrazines
Liu, Nai-Wei,Liang, Shuai,Manolikakes, Georg
supporting information, p. 1308 - 1319 (2017/04/18)
A photoredox-catalyzed three-component synthesis of N-aminosulfonamides starting from diaryliodonium salts, hydrazines and sulfur dioxide is reported. This reaction proceeds under mild conditions at room temperature and is driven by visible light. A simple bisulfite salt can be used as a readily available and easy-to-handle sulfur dioxide source. Mechanistic studies support a catalytic photoredox pathway with the diaryliodonium salt as convenient source for aryl radicals. (Figure presented.).
A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO2 Source
Van Mileghem, Seger,De Borggraeve, Wim M.
supporting information, p. 785 - 787 (2017/05/29)
A convenient synthesis of DABCO·(SO2)2 (abbreviated as DABSO) is reported. Using a two-chamber setup, sulfur dioxide is generated in one chamber and consumed in the other. This closed system overcomes safety issues related to working
A palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines
An, Yuanyuan,Xia, Hongguang,Wu, Jie
supporting information, p. 1665 - 1669 (2016/02/09)
A facile route to synthesise N-aminosulfonamides through a palladium-catalyzed coupling reaction of aryl nonaflates, sulfur dioxide, and hydrazines is reported. This transformation proceeds in the presence of Pd(OAc)2/XantPhos, and TBAB in 1,4-dioxane at 80°C, leading to the corresponding N-aminosulfonamides in moderate to good yields. The reaction scope has been demonstrated, and good functional tolerance is observed. A plausible mechanism is proposed through the insertion of sulfur dioxide.
Palladium-catalyzed aminosulfonylation of aryl iodides by using Na 2SO3 as the SO2 source
Li, Wanfang,Li, Haoquan,Langer, Peter,Beller, Matthias,Wu, Xiao-Feng
supporting information, p. 3101 - 3103 (2014/06/09)
We realized an interesting palladium-catalyzed aminosulfonylation of aryl iodides by using Na2SO3 as a cheap SO2 source. In most cases, the yields were comparable to those reported by using the 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABCO·2SO 2, DABSO) as the SO2 source. Copyright
A copper-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines
Wang, Xianbo,Xue, Lijun,Wang, Zhiyong
supporting information, p. 4056 - 4058 (2014/08/18)
A three-component reaction of triethoxysilanes, sulfur dioxide, and hydrazines catalyzed by copper(II) acetate is reported, leading to N-aminosulfonamides in good yields. Not only triethoxy(aryl)silanes but also triethoxy(alkyl)silanes are compatible during the process of insertion of sulfur dioxide. Additionally, diethoxydiarylsilanes are suitable under the conditions as well.
Aminosulfonylation of aromatic amines, sulfur dioxide and hydrazines
Zheng, Danqing,Li, Ying,An, Yuanyuan,Wu, Jie
supporting information, p. 8886 - 8888 (2014/08/05)
A facile route to aryl N-aminosulfonamides under mild conditions is provided. The reaction of aromatic amines (including heteroaromatic amines), sulfur dioxide, and hydrazines proceeds efficiently with good functional group tolerance. The in situ generated diazonium ion is involved in the aminosulfonylation process. This journal is the Partner Organisations 2014.
Metal-free aminosulfonylation of aryldiazonium tetrafluoroborates with DABCO×(SO2)2 and hydrazines
Zheng, Danqing,An, Yuanyuan,Li, Zhenhua,Wu, Jie
supporting information, p. 2451 - 2454 (2014/03/21)
The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO 2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds smoothly at room temperature and shows broad functional-group tolerance. A radical process is proposed for this transformation. The coupling of aryldiazonium tetrafluoroborates, DABCO×(SO2)2, and hydrazines under metal-free conditions leads to the formation of aryl N-aminosulfonamides. The reaction proceeds under mild reaction conditions, is fast, has a broad substrate scope, and gives the products in high yiels (21 examples). A plausible mechanism that involves a radical process is also proposed. Copyright
One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation
Richards-Taylor, Charlotte S.,Blakemore, David C.,Willis, Michael C.
, p. 222 - 228 (2014/01/06)
A palladium-catalysed aminosulfonylation process is used as the key-step in a one-pot, three-component sulfone synthesis. The process combines aryl-, heteroaryl- and alkenyl iodides with a sulfonyl unit and an electrophilic coupling fragment. The sulfonyl unit is delivered in the form of an aminosulfonamide, which then serves as a masked sulfinate. The sulfinate is combined, in situ, with an electrophilic coupling partner, such as a benzylic, allylic or alkyl halide, an electron-poor arene, or a cyclic epoxide, to provide the corresponding sulfone products in good to excellent yields. The mild reaction conditions and use of commercially available reaction components allows the easy preparation of a broad range of sulfones featuring a variety of functional groups. The process obviates the need to employ thiol starting materials, and oxidative operations.
