28823-18-9Relevant academic research and scientific papers
Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols
Ma, Jinfeng,Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, (2021/10/26)
A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.
An iodine-mediated new avenue to sulfonylation employingN-hydroxy aryl sulfonamide as a sulfonylating agent
Raghuvanshi, Dushyant Singh,Verma, Narsingh
supporting information, p. 4760 - 4767 (2021/06/09)
A novel and highly efficient I2/K2CO3mediated regioselective sulfonylation of thiophenols, aryl acetylenic acid and aromatic alkynes withN-hydroxy sulfonamide has been developed.N-hydroxy sulfonamide has been used for the first time for the synthesis of these sulfones. The scope and versatility of the reaction has been demonstrated by the regio- and stereoselective synthesis of different analogs of sulfones with various structural features.
Atom transfer radical addition to styrenes with thiosulfonates enabled by synergetic copper/photoredox catalysis
Zhou, Xin,Peng, Zhiyuan,Wang, Peng George,Liu, Qingchao,Jia, Tiezheng
supporting information, p. 1054 - 1059 (2021/02/01)
A synergetic copper/photoredox catalyzed ATRA of styrenes and thiosulfonates is developed. Besides aryl ethylenes, the challenging α-substituted styrenes were employed to construct the benzylic quaternary carbon centers. Owing to the mild conditions as well as the high level of substrate compability, this ATRA could be applied to derivatize bioactive natural products in late stage, and to install fluorophores across alkenes. The mechanistic studies reveal sulfonyl radicals as the key intermediate in the transformation.
Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates
Dong, Yue,Ji, Peng,Zhang, Yueteng,Wang, Changqing,Meng, Xiang,Wang, Wei
supporting information, p. 9562 - 9567 (2021/01/09)
A mild organophotoredox synthetic protocol for forming a Csp3-S/Se bond by reacting widespread redox-active esters with thio/selenosulfonates has been developed. The power of the synthetic manifold is fueled by an unprecedented broad substrate scope and wide functional group tolerance.
TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols: Construction of thiosulfonate under transition-metal free conditions
Huang, Cheng-Mi,Li, Jian,Wang, Shun-Yi,Ji, Shun-Jun
supporting information, p. 1923 - 1926 (2020/01/13)
A TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols to construct thiosulfonates under transition-metal free conditions is reported. The thiosulfonates were isolated in good yields with broad tolerance of function
Electrochemical Oxidative Cross-Coupling Reaction to Access Unsymmetrical Thiosulfonates and Selenosulfonates
Zhang, Xiaofeng,Cui, Ting,Zhang, Yanghao,Gu, Weijin,Liu, Ping,Sun, Peipei
, p. 2014 - 2019 (2019/03/26)
The electrochemical oxidative cross-dehydrogenative coupling of arylsulfinic acids with thiophenols was achieved via a radical process. A wide range of arylsulfinic acids and substituted thiophenols were found to be tolerated, providing unsymmetrical thio
Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
Zhang, Yueteng,Ji, Peng,Hu, Wenbo,Wei, Yongyi,Huang, He,Wang, Wei
supporting information, p. 8225 - 8228 (2019/07/16)
A metal- and oxidant-free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10-phenanthrenequinone-promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late-stage modification of complex structures, which are difficult to achieve with the existing protocols.
Unprecedented Reactivity of β-Iodovinyl Sulfones: An Efficient Synthesis of β-Keto Sulfones and β-Keto Thiosulfones
Reddy, Raju Jannapu,Kumar, Jangam Jagadesh,Kumari, Arram Haritha
supporting information, p. 3771 - 3775 (2019/06/24)
An unprecedented reactivity of (E)-β-iodovinyl sulfones in the presence of NaOAc is reported. The (E)-β-iodovinyl sulfones were treated with NaOAc in DMSO/H2O to yield β-keto sulfones in moderate to high yields. A novel oxidative difunctionalization of β-iodovinyl sulfones with thiosulfonates and NaOAc in DMF has been developed. This metal-free oxosulfenylation is an operationally simple to access a wide range of β-keto thiosulfones (α-thioaryl-β-keto sulfones) in moderate to high yields. The transformations were reliable at gram-scale, thus illustrating its efficiency and practicality. A plausible mechanism for the protocol is also proposed.
Metal-Free Synthesis of Thiosulfonates via Insertion of Sulfur Dioxide
Li, Guoqing,Gan, Ziyu,Kong, Kexin,Dou, Xiaomeng,Yang, Daoshan
supporting information, p. 1808 - 1814 (2019/03/28)
A simple and catalyst-free strategy was developed for the synthesis of unsymmetrical thiosulfonates using readily available DABCO?(SO2)2 as a solid and bench-stable sulfur dioxide surrogate. The corresponding thiosulfonates were obtained through a radical pathway with good functional group tolerance. This strategy offers a promising synthesis method for the construction of diverse and useful thiosulfonates in the field of synthetic and pharmaceutical chemistry and extends the number of still limited sulfur dioxide fixation strategies. (Figure presented.).
Ammonium iodide-mediated electrosynthesis of unsymmetrical thiosulfonates from arenesulfonohydrazides and thiols
Terent'ev, Alexander O.,Mulina, Olga M.,Ilovaisky, Alexey I.,Kokorekin, Vladimir A.,Nikishin, Gennady I.
, p. 80 - 82 (2019/02/20)
Unsymmetrical thiosulfonates were synthesized from thiols and arenesulfonohydrazides by their electrolysis in undivided cell equipped with graphite anode and stainless steel cathode under high current density applying NH4I both as a redox catal
