959312-83-5Relevant articles and documents
Synthesis of 2-(Arylthio)indolenines via Chemoselective Arylation of Thio-Oxindoles with Arynes
Saputra, Adi,Fan, Rong,Yao, Tuanli,Chen, Jian,Tan, Jiajing
, p. 2683 - 2688 (2020/05/18)
A chemoselective S-arylation reaction of thio-oxindoles with arynes is presented. The reaction was performed under mild conditions and provided a straightforward synthesis of 2-(arylthio)indolenines in good to excellent yields. Besides, this simple operat
Multifunctionalization of Indoles: Synthesis of 3-Iodo-2-sulfonyl Indoles
Park, Hyowon,Bae, Junryeol,Son, Soobin,Jang, Hye-Young
, p. 1128 - 1133 (2019/11/22)
The selective multifunctionalization of indoles by using thiosulfonates, trimethyl sulfoxonium iodide (Me3SOI), and H2O2 was studied. The reaction of thiosulfonates with Me3SOI and H2O2 produced sulfonyl radicals and an iodination reagent, both of which were incorporated in indoles to form 3-iodo-2-sulfonyl indoles under carefully controlled conditions. The related reaction mechanism and the substrate scope of 3-iodo-2-sulfonyl indoles are presented.
The fast and efficient KI/H2O2 mediated 2-sulfonylation of indoles and N-methylpyrrole in water
Zhang, Jun,Wang, Zhong,Chen, Lingjuan,Liu, Yan,Liu, Ping,Dai, Bin
, p. 41651 - 41656 (2019/01/03)
The rapid and efficient KI/H2O2-mediated 2-sulfonylation of substituted indoles and N-methylpyrrole was established. The corresponding 2-sulfonylation products are synthesized from readily available sulfur sources, namely arylsulfonyl hydrazides, 4-methylbenzenesulfinic acid and sodium 4-methylbenzenesulfinate in good to excellent yields in only 5 min. Moreover, the aqueous solution of hydrogen peroxide is used as both oxidant and solvent. Mechanistic studies demonstrated that 2,3-diiodoindoline was the main sulfonylation intermediate.
Electrooxidative Metal-Free Dehydrogenative α-Sulfonylation of 1H-Indole with Sodium Sulfinates
Feng, Mei-Lin,Xi, Long-Yi,Chen, Shan-Yong,Yu, Xiao-Qi
, p. 2746 - 2750 (2017/05/29)
A method for the electrochemical α-sulfonylation of 1H-indole with arenesulfinates was developed. A variety of indoles underwent this sulfonylation smoothly at room temperature under metal-free and chemical-oxidant-free conditions to afford indolyl aryl sulfones in good to high yields. This reaction was found to tolerate a variety of functional groups, including halides and cyclopropyl, ether, ester, and aldehyde groups. It was applied to the synthesis of biologically active 5-HT6 modulators.
A Sulfonylation Reaction: Direct Synthesis of 2-Sulfonylindoles from Sulfonyl Hydrazides and Indoles
Rahaman, Rajjakfur,Barman, Pranjit
supporting information, p. 684 - 690 (2017/03/21)
A metal-free synthesis of 2-sulfonylindole derivatives has been developed through a novel TBHP/I2-mediated coupling of C3/unsubstituted indoles with sulfonyl hydrazides. The reaction utilizes readily available starting materials under mild reaction conditions, providing an alternative and attractive approach to 2-sulfonylindoles with high yields. The developed synthetic procedure is suitable for both N-protected or unprotected indoles.
Convenient KI-catalyzed regioselective synthesis of 2-sulfonylindoles using water as solvent
Li, Hongjie,Wang, Xiaolong,Yan, Jie
supporting information, p. 4277 - 4280 (2017/07/11)
A convenient procedure is developed for the preparation of 2-sulfonylindoles from indoles and sodium sulfinates catalyzed by KI in water. This environmentally benign 2-sulfonylation of indoles proceeds efficiently under mild conditions, affording the products with high regioselectivity and in moderate to good yields.
Catalyst-controlled selectivity in C-S bond formation: Highly efficient synthesis of C2- and C3-sulfonylindoles
Yang, Yong,Li, Wanmei,Xia, Chengcai,Ying, Beibei,Shen, Chao,Zhang, Pengfei
, p. 304 - 307 (2016/02/05)
Exploring a potential catalyst system for catalyst-controlled selectivity in C-S bond formation is a fascinating challenge. Herein, we described two novel and highly efficient methods for the selective synthesis of C2- and C3-sulfonylindoles showing good biological activities by employing iodide and copper catalysts, respectively. Mechanistic studies point to the crucial role of the electronic properties of the sulfonylated intermediates. I see two and I see three: Two novel and highly efficient methods for the selective synthesis of C2- and C3-sulfonylindoles by employing iodide and copper catalysts, respectively, are described. Mechanistic studies point to the crucial role of the electronic properties of the sulfonylated intermediates. phen=1,10-phenantroline, TBHP=tert-butyl hydroperoxide.
Regioselective C 2 sulfonylation of indoles mediated by molecular iodine
Katrun, Praewpan,Mueangkaew, Charoensak,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
, p. 1778 - 1785 (2014/03/21)
A facile and general method for regioselective C2 sulfonylation reaction of indoles mediated by iodine is described. The 2-sulfonylated products were obtained up to 96% yield under mild reaction conditions (room temperature, 2 h).
Iodine-catalyzed regioselective 2-sulfonylation of indoles with sodium sulfinates
Xiao, Fuhong,Chen, Hui,Xie, Hao,Chen, Shuqing,Yang, Luo,Deng, Guo-Jun
supporting information, p. 50 - 53 (2014/01/23)
Iodine-catalyzed selective 2-arylsulfonyl indole formation from indoles and sodium sulfinates is disclosed. Various substituted 2-arylsulfonyl indoles were obtained in one pot in the absence of metal catalyst at room temperature under air.
Rh2(II)-catalyzed nitro-group migration reactions: Selective synthesis of 3-nitroindoles from β-nitro styryl azides
Stokes, Benjamin J.,Liu, Sheng,Driver, Tom G.
, p. 4702 - 4705 (2011/05/16)
Rhodium carboxylate complexes (1 mol %) catalyze the migration of electron-withdrawing groups to selectively produce 3-substituted indoles from β-substituted styryl azides. The relative order of migratorial aptitude for this transformation is ester ? amide H sulfonyl benzoyl ? nitro.
