1483-92-7Relevant academic research and scientific papers
Synthesis, Crystal Structure and Electronic Properties of a 2Fe-2S Complex with a Bulky Thiolato Ligand, 2
Ueyama, Norikazu,Ueno, Satoru,Sugawara, Takashi,Tatsumi, Kazuyuki,Nakamura, Akira,Yasuoka, Noritake
, p. 2723 - 2728 (1991)
The complex 2 (tmbt = 2,4,6-trimethylbenzenethiolate) was synthesised and its molecular structure determined.The crystal system is monoclinic with a = 15.241(6), b = 16.174(5), c = 16.768(6) Angstroem, β = 135.84(2) deg and Z = 2, in s
Nonheme iron-thiolate complexes as structural models of sulfoxide synthase active sites
Ekanayake, Danushka M.,Fischer, Anne A.,Elwood, Maya E.,Guzek, Alexandra M.,Lindeman, Sergey V.,Popescu, Codrina V.,Fiedler, Adam T.
, p. 17745 - 17757 (2020)
Two mononuclear iron(ii)-thiolate complexes have been prepared that represent structural models of the nonheme iron enzymes EgtB and OvoA, which catalyze the O2-dependent formation of carbon-sulfur bonds in the biosynthesis of thiohistidine compounds. The series of Fe(ii) complexes reported here feature tripodal N4 chelates (LA and LB) that contain both pyridyl and imidazolyl donors (LA = (1H-imidazol-4-yl)-N,N-bis((pyridin-2-yl)methyl)methanamine; LB = N,N-bis((1-methylimidazol-2-yl)methyl)-2-pyridylmethylamine). Further coordination with monodentate aromatic or aliphatic thiolate ligands yielded the five-coordinate, high-spin Fe(ii) complexes [FeII(LA)(SMes)]BPh4 (1) and [FeII(LB)(SCy)]BPh4 (2), where SMes = 2,4,6-trimethylthiophenolate and SCy = cyclohexanethiolate. X-ray crystal structures revealed that 1 and 2 possess trigonal bipyramidal geometries formed by the N4S ligand set. In each case, the thiolate ligand is positioned cis to an imidazole donor, replicating the arrangement of Cys- and His-based substrates in the active site of EgtB. The geometric and electronic structures of 1 and 2 were analyzed with UV-vis absorption and M?ssbauer spectroscopies in tandem with density functional theory (DFT) calculations. Exposure of 1 and 2 to nitric oxide (NO) yielded six-coordinate FeNO adducts that were characterized with infrared and electron paramagnetic resonance (EPR) spectroscopies, confirming that these complexes are capable of binding diatomic molecules. Reaction of 1 and 2 with O2 causes oxidation of the thiolate ligands to disulfide products. The implications of these results for the development of functional models of EgtB and OvoA are discussed. This journal is
Lewis base-complexed magnesium dithiolenes
Wang, Yuzhong,Maxi, Nirva A.,Xie, Yaoming,Wei, Pingrong,Schaefer, Henry F.,Robinson, Gregory H.
, p. 8087 - 8089 (2019)
The first magnesium-based dithiolene, 2, was prepared by reaction of the lithium dithiolene radical, 1, with 2-mesitylmagnesium bromide. Reaction of 2 with N-heterocyclic carbenes (in toluene) gave a carbene-stabilized magnesium monodithiolene complex, 3. Complex 3, in turn, is readily converted to a THF-solvated magnesium bis-dithiolene dianion, 4, via partial hydrolysis in polar solvents (i.e., THF/CH3CN). Compounds 2, 3 and 4 have been spectroscopically and structurally characterized and probed by DFT computations.
Synthesis and crystal structure of an arenesulfenyl iodide with unprecedented stability
Goto, Kei,Holler, Michel,Okazaki, Renji
, p. 1915 - 1916 (1998)
An arenesulfenyl iodide with unprecedented stability was synthesized by oxidation of a thiol bearing a novel bowl-type substituent with iodine, whose monomeric structure was determined by X-ray crystallographic analysis.
Synthesis of Symmetrical Thiosulfonates via Cu(OTf)2-Catalyzed Reductive Homocoupling of Arenesulfonyl Chlorides
Liu, Lixia,Luo, Bo,Wang, Chengming
supporting information, p. 5880 - 5883 (2021/11/27)
A variety of symmetrical thiosulfonates are synthesized via Cu-catalyzed reductive homocoupling of aryl sulfonyl chlorides. This protocol uses organic amine acting as a mild reductant and low-cost copper as an effective catalyst. Such a reductive coupling process features a broad substrate scope and good functional group tolerance. Related thiosulfonate products can also be converted into diverse functional molecules.
Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst
Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming
supporting information, p. 6059 - 6064 (2021/08/23)
Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.
Synthesis of symmetrical / unsymmetrical thiosulfonates through the disproportionate coupling reaction of sulfonyl hydrazide mediated by phosphomolybdic acid
Lv, Mengting,Liu, Yufeng,Li, Ke,Yang, Guoping
supporting information, (2021/01/21)
Phosphomolybdic acid (H3PMo12O40) is reported as a green low-cost catalyst for the synthesis of symmetrical / unsymmetrical thiosulfonates via the disproportionate coupling reaction of sulfonyl hydrazide. The attributes of this reported catalytic system include low catalyst loadings (1 mol%), efficient turnover, and high yields (up to 94%). Additionally, this reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via sulfinyl radical disproportionation.
Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2
Leng, Jing,Wang, Shi-Meng,Qin, Hua-Li
supporting information, p. 903 - 909 (2017/06/23)
A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.
Preparation of Propargylic Sulfinates and their [2,3]-Sigmatropic Rearrangement to Allenic Sulfones
Tata, Rama Rao,Hampton, Carissa S.,Harmata, Michael
supporting information, p. 1232 - 1241 (2017/04/11)
The scope of the [2,3]-sigmatropic rearrangement of propargylic sulfinates to allenic sulfones by silver catalysis was expanded. A series of new propargylic sulfinate esters was generated from a variety of aromatic and heteroaromatic sulfonyl chlorides an
Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide
Zheng, Yong,Qing, Feng-Ling,Huang, Yangen,Xu, Xiu-Hua
supporting information, p. 3477 - 3481 (2016/11/13)
A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).
