- Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles
-
A visible-light-induced radical domino reaction of 1-allyl-2-ethynylbenzoimidazoles with thiosulfonates was developed, which generated the thiosulfonylated pyrrolo[1,2-a]benzimidazoles in moderate to good yields. This reaction proceeded under transition-metal-free conditions with good functional group tolerance and high regioselectivity. The possible pathway involved thiosulfonates were activated through the energy transfer route promoted by photocatalysis.
- Liu, Yan,Zhang, Niuniu,Xu, Yanli,Chen, Yanyan
-
p. 16882 - 16891
(2021/11/18)
-
- Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols
-
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.
- Ma, Jinfeng,Xu, Pan,Zhong, Zijian,Zhou, Aihua
-
supporting information
(2021/10/26)
-
- An iodine-mediated new avenue to sulfonylation employingN-hydroxy aryl sulfonamide as a sulfonylating agent
-
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.
- Raghuvanshi, Dushyant Singh,Verma, Narsingh
-
supporting information
p. 4760 - 4767
(2021/06/09)
-
- The organocatalytic synthesis of perfluorophenylsulfides: Via the thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates
-
The organic superbase t-Bu-P4-catalyzed direct thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates was developed. Yields of perfluorophenylsulfides of up to 97% under catalysis of 5 mol% t-Bu-P4 were achieved. This method was shown to provide an efficient way to construct the perfluorophenyl-sulfur bond under mild metal-free reaction conditions. This journal is
- Cai, Zhihua,Du, Guangfen,He, Lin,Lin, Muze,Luo, Jinyun,Wu, Leifang
-
supporting information
p. 9237 - 9241
(2021/11/13)
-
- Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives
-
A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.
- Chen, Hui,Chen, Yanyan,Mo, Zuyu,Xu, Yanli,Yan, Yunyun,Zhang, Niuniu
-
supporting information
p. 376 - 381
(2021/01/13)
-
- Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates andN-substituted formamides
-
A general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates starting from thiosulfonates andN-substituted formamides is developed. By employing rhodamine B as a photocatalyst andtert-butyl hydroperoxide (TBHP) as an oxidant, a wide scope of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under irradiation of blue light at room temperature for 12 h.
- Bi, Wen-Zhu,Zhang, Wen-Jie,Li, Zi-Jie,He, Yuan-Hao,Feng, Su-Xiang,Geng, Yang,Chen, Xiao-Lan,Qu, Ling-Bo
-
supporting information
p. 8701 - 8705
(2021/10/22)
-
- Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
-
A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
- Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
-
p. 6600 - 6604
(2020/09/02)
-
- Visible-light induced decarboxylative coupling of redox-active esters with disulfides to construct C-S bonds
-
A novel method has been established for the construction of C-S bonds using redox-active esters with disulfides in the presence of Ru-photoredox catalyst. This method exhibits remarkable functional group tolerance across a wide scope of substrates. Under
- Xiao, Zhiwei,Wang, Lu,Wei, Junjie,Ran, Chongzhao,Liang, Steven H.,Shang, Jingjie,Chen, Guang-Ying,Zheng, Chao
-
supporting information
p. 4164 - 4167
(2020/04/22)
-
- Nickel-Catalyzed Defluorinative Reductive Cross-Coupling Reaction of gem-Difluoroalkenes with Thiosulfonate or Selenium Sulfonate
-
A nickel-catalyzed defluorinative reductive cross-coupling of gem-difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high E-selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.
- Li, Jian,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun
-
p. 11542 - 11552
(2019/09/30)
-
- Metal-Free Synthesis of Thiosulfonates via Insertion of Sulfur Dioxide
-
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.).
- Li, Guoqing,Gan, Ziyu,Kong, Kexin,Dou, Xiaomeng,Yang, Daoshan
-
supporting information
p. 1808 - 1814
(2019/03/28)
-
- Method for synthesizing thiosulfonate compounds on the basis of strategy of SO2 insertion
-
The invention relates to a method for synthesizing thiosulfonate compounds on the basis of strategy of SO2 insertion. The method includes: performing a reaction in the presence of nitrogen gas and atcertain temperature to prepare the thiosulfonate compoun
- -
-
Paragraph 0044; 0045; 0046; 0047; 0048
(2019/04/26)
-
- Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides
-
A highly efficient sulfonylation of thiols has been achieved through the metal-free NaI/TBHP-mediated cross-coupling of sulfonyl hydrazides and thiols at room temperature. This method provides a convenient and practical route to thiosulfonates in 84-99% y
- Chen, Qian,Huang, Yulin,Wang, Xiaofeng,Wu, Jiawei,Yu, Guodian
-
p. 1713 - 1719
(2018/03/21)
-
- Electrochemical sulfonylation of thiols with sulfonyl hydrazides: A metal- and oxidant-free protocol for the synthesis of thiosulfonates
-
An efficient electrochemical transformation of structurally diverse sulfonyl hydrazides and thiols into thiosulfonates in the presence of ammonium iodide as redox catalyst and electrolyte in acetonitrile at ambient temperature is reported. Transition metal- and oxidant-free conditions are the striking features of this protocol. The in vitro cytotoxicity of all compounds is evaluated by MTT assay against four human cancer cell lines. The results reveal that 3ac and 3ag exhibit potential inhibitory activity against tumor cells. Furthermore, 3ag inhibits cell migration ability and tubulin polymerization in T-24 cells, leading to cell cycle arrest and apoptosis.
- Mo, Zu-Yu,Swaroop, Toreshettahally R.,Tong, Wei,Zhang, Yu-Zhen,Tang, Hai-Tao,Pan, Ying-Ming,Sun, Hong-Bin,Chen, Zhen-Feng
-
supporting information
p. 4428 - 4432
(2018/10/17)
-
- PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
-
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.
- Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
-
p. 2360 - 2364
(2018/05/24)
-
- Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
-
A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
- Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
-
supporting information
p. 2808 - 2811
(2016/07/06)
-
- Facile synthesis of symmetric thiosulfonates by oxidation of disulfide with oxone/MX (MX = KBr, KCl, NaBr and NaCl)
-
Abstract A new method is described for the oxidation of aliphatic- and aromatic disulfides containing electron-donating and electron-withdrawing groups to their corresponding thiosulfonates using oxone in combination with the MX (MX = KBr, KCl, NaBr and NaCl). No obvious electronic effects influence the yields of thiosulfonates. Avoiding the usage of toxic and unstable reagents, mild reaction conditions, short reaction times and cost-effectiveness are advantages of this methodology when likened to known methods for thiosulfonates syntheses.
- Natarajan, Palani
-
p. 4131 - 4134
(2015/08/03)
-
- Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water
-
The first example of Sc(OTf)3-catalyzed sulfenylation of sodium sulfinates with N-(organothio)succinimides in ionic liquids (ILs) and water cosolvent system was developed, achieving thiosulfonates in moderate to excellent yields. Additionally, Sc(OTf)3/ILs could be recovered easily after the reactions and reused without a significant loss in the catalytic activity. Thus, the present protocol represents an interesting complement to known methods for thiosulfonates synthesis.
- Liang, Gaigai,Chen, Jing,Chen, Jiali,Li, Wanmei,Chen, Jiuxi,Wu, Huayue
-
supporting information
p. 6768 - 6770
(2013/01/15)
-
- NBS-promoted sulfenylation of sulfinates with disulfides leading to unsymmetrical or symmetrical thiosulfonates
-
A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS-promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom-economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disulfides generating N-(organothio)succinimide that then undergos facile sulenylation with sulfinates is proposed. Copyright
- Liang, Gaigai,Liu, Miaochang,Chen, Jiuxi,Ding, Jinchang,Gao, Wenxia,Wu, Huayue
-
experimental part
p. 1611 - 1616
(2012/09/07)
-
- Hypervalent iodine in synthesis. XXII: A novel way for the preparation of unsymmetric S-aryl thiosulfonates by the reaction of potassium thiosulfonates with diaryliodonium salts
-
Unsymmetric S-aryl thiosulfonates can be generated through a novel way for the reaction of potassium thiosulfonates with diaryliodonium salts in good yields under mild conditions.
- Xia, Min,Chen, Zhen-Chu
-
p. 1309 - 1313
(2007/10/03)
-
- REACTION OF N-ARYLTHIO-1,4-BENZOQUINONE IMINES WITH BENZENESULFINIC ACID
-
In reaction with sodium benzenesulfinate in acetic acid benzoquinone imines containing a RC6H4S (R = H, 4-OCH3, 4-Cl, 4-NO2, 2-NO2) group at the nitrogen atom form aryl benzenethiosulfonates and the benzenesulfinate of 2-phenylsulfonyl-4-aminophenol.The introduction of two nitro groups into the phenylthio group creates conditions for reaction in the quinonoid fragment, and here the main products are N-(2,4-dinitrophenylthio)-2(3)-phenylsulphonyl-4-aminophenols.
- Kolesnikov, V. T.,Vid, L. V.,Kuz'menko, L. O.
-
p. 1906 - 1909
(2007/10/02)
-