80472-59-9Relevant academic research and scientific papers
Acid-Mediated Sulfonylthiolation of Arenes via Selective Activation of SS-Morpholino Dithiosulfonate
Kanemoto, Kazuya,Furuhashi, Koudai,Morita, Yoshitsugu,Komatsu, Teruyuki,Fukuzawa, Shin-Ichi
, p. 1582 - 1587 (2021)
A trifluoroacetic-acid-mediated desulfurilative sulfonylthiolation of arenes using SS-morpholino dithiosulfonate is described. This system is based on selective activation of the morpholino group over the tosyl group of the doubly transformable sulfur surrogate. Mechanistic studies suggested that the reaction proceeds through electrophilic aromatic substitution followed by sulfur extrusion. The wide substrate scope of this reaction and the transformability of the resulting thiosulfonates enable expeditious access to divergent multifunctionalized sulfides.
Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes
Kumari, Arram Haritha,Kumar, Jangam Jagadesh,Krishna, Gamidi Rama,Reddy, Raju Jannapu
supporting information, p. 2850 - 2864 (2021/05/18)
An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.
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.
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
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.
Selective Ortho Thiolation Enabled by Tuning the Ancillary Ligand in Palladium/Norbornene Catalysis
Cai, Wenqiang,Gu, Zhenhua
supporting information, p. 3204 - 3209 (2019/05/01)
Site-selective introduction of a sulfur group into aromatic compounds is essential and useful in organic, material, and pharmaceutical chemistry. A palladium/norbornene-catalyzed chemoselective ortho thiolation of aryl halides was reported. The selectivit
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
Unsymmetrical Organotrisulfide Formation via Low-Temperature Disulfanyl Anion Transfer to an Organothiosulfonate
Ali, Doaa,Hunter, Roger,De Doncker, Stephen,Rees-Jones, Sophie C. M.,Kaschula, Catherine H.
, p. 2862 - 2869 (2019/03/23)
New methodology is presented for the formation of unsymmetrical organotrisulfides in a high yield and purity, relatively free of polysulfide byproducts. The highlight of the method is the low-temperature (-78 °C) deprotection of a disulfanyl acetate with sodium methoxide in THF to form a disulfanyl anion, which reacts rapidly in situ with an organothiosulfonate (S-aryl or S-alkyl) within 30 seconds followed by quenching. The discovery of these new reaction conditions together with the relative greenness of the chemistry overall makes for an efficient protocol, from which a range of organotrisulfides covering aliphatic, aromatic, as well as cysteine and sugar groups can be accessed in a high yield and purity.
PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
, p. 2360 - 2364 (2018/05/24)
A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
H2O2-mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400
Peng, Zhihong,Zheng, Xiao,Zhang, Yingjun,An, Delie,Dong, Wanrong
supporting information, p. 1760 - 1764 (2018/04/30)
A green and practical protocol between sulfonyl hydrazides and disulfides is herein reported for the synthesis of unsymmetrical thiosulfonates with the assistance of H2O2 in PEG-400, releasing N2 and H2O as the byproducts. The efficient and compatible process was considered to take place in the absence of metallic catalysts through a radical mechanism as determined by EPR analysis.
