52920-45-3Relevant academic research and scientific papers
Metal-Free Synthesis of β-Bromoalkenyl Sulfides via Deoxygenative Bromination/Olefination/Sulfenylation of Ketones with Sulfonyl Hydrazides and Pyridinium Tribromide
Bao, Yishu,Zhong, Lingyu,Hou, Qiaodan,Zhou, Qingfa,Yang, Fulai
, p. 1063 - 1068 (2018)
A novel metal-free method for synthesis of β-bromoalkenyl sulfides via deoxygenative bromination/olefination/sulfenylation process using commercially available ketones, sulfonyl hydrazides and pyridinium tribromide as starting materials has been developed. In this reaction, pyridinium tribromide plays the role of oxidant and substrate, wherein water and molecular nitrogen are generated as environmentally benign by-products. Preliminary investigation revealed that vinyl bromides were critical intermediate. Importantly, this protocol not only obviates the use of alkynes and traditional sulfenylating agents, but also reveals that ketones can be used as precursors of vinyl bromides.
Solvent-Driven Mono- and Bis-sulfenylation of (E)-β-Iodovinyl Sulfones with Thiols for Flexible Synthesis of 1,2-Thiosulfonylalkenes and 1,2-Dithioalkenes
Reddy, Raju Jannapu,Kumari, Arram Haritha,Sharadha, Nunavath,Krishna, Gamidi Rama
supporting information, p. 3934 - 3951 (2022/03/16)
The nature of solvent is a key factor for stereoselective mono- and bis-thiolation of (E)-β-iodovinyl sulfones with thiols under basic conditions. A novel and unprecedented vicinal bisthiolation of (E)-β-iodovinyl sulfones with thiols under the influence of K2CO3/DMSO at room temperature for quick assembly of (E)-1,2-dithio-1-alkenes is presented. Solvent-induced stereoselective monosulfenylation of (E)-β-iodovinyl sulfones with thiols has also been established for the synthesis of both (E)- and (Z)-1,2-thiosulfonylethenes in MeCN and MeOH, respectively. Moreover, K2CO3-mediated desulfonylative-sulfenylation of (Z)-1,2-thiosulfonylethenes with thiols in DMSO furnished unsymmetrical (Z)-1,2-dithio-1-alkenes for the first time. The solvent-dependent versatile reactivity of (E)-β-iodovinyl sulfones has been successfully explored to provide a set of (E)-/(Z)-1,2-dithio-1-alkenes and (E)-/(Z)-1,2-thiosulfonyl-1-alkenes in good to high yields with excellent stereoselectivities. Notably, this operationally simple process utilizes a broad substrate scope with good functional group tolerance and compatibility. The efficacy of the process has been proven for gram-scale reactions, and plausible mechanistic models are outlined on the basis of experimental results and control experiments.
Generation of β-Halo Vinylsulfones through a Multicomponent Reaction with Insertion of Sulfur Dioxide
Xiang, Yuanchao,Kuang, Yunyan,Wu, Jie
, p. 6996 - 6999 (2017/05/29)
A four-component reaction of terminal alkynes, aryldiazonium tetrafluoroborates, sulfur dioxide surrogate of DABCO?(SO2)2, and potassium halide in the presence of copper(I) chloride (10 mol %) gives rise to β-halo vinylsulfones with good stereoselectivity. The vicinal difunctionalization of alkynes through sulfonylation and halogenation with the insertion of sulfur dioxide works efficiently. A plausible mechanism is proposed, which includes a radical process.
Aerobic copper-catalyzed synthesis of (E)-alkenyl sulfones and (E)-β-halo-alkenyl sulfones via addition of sodium sulfinates to alkynes
Taniguchi, Nobukazu
supporting information, p. 1984 - 1990 (2014/03/21)
Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the reaction using CuI catalyst produced (E)-β-haloalkenyl sulfones anti-selectively in the presence of potassium halides. Furthermore, the (E)-β-bromoalkenyl sulfones are possible to convert into various alkenyl sulfones by Suzuki-Miyaura coupling.
Iron halide-mediated regio- and stereoselective halosulfonylation of terminal alkynes with sulfonylhydrazides: Synthesis of (E)-β-chloro and bromo vinylsulfones
Li, Xiaoqing,Shi, Xinhua,Fang, Mingwu,Xu, Xiangsheng
, p. 9499 - 9504 (2013/10/08)
Halosulfonylation of terminal alkynes was achieved with sulfonylhydrazides as the sulfonyl precursor and inexpensive iron halide as halide source in the presence of TBHP, allowing the regio- and stereoselective generation of (E)-β-chloro and bromo vinylsu
Convenient ambient temperature generation of sulfonyl radicals
Gilmore, Kerry,Gold, Brian,Clark, Ronald J.,Alabugin, Igor V.
, p. 336 - 340 (2013/05/08)
Presented herein is a novel method for the efficient, ambient temperature generation of sulfonyl radicals from aryl and alkyl sulfonylbromides upon autoxidation of triethylborane (Et3B). The resultant radicals were regioselectively trapped via addition to terminal alkynes, generating a secondary vinyl radical that selectively abstracts a Br atom from RSO 2Br, yielding the (E)-bromo vinylsulfones. Sensitivity towards Lewis basic groups was observed, presumably due to the disruptive coordination to Et3B before atom-transfer.
Stereoselective synthesis of (E)-alkenyl sulfones from alkenes or alkynes via copper-catalyzed oxidation of sodium sulfinates
Taniguchi, Nobukazu
supporting information; experimental part, p. 1308 - 1312 (2011/07/07)
Alkenyl sulfones can be stereoselectively synthesized from alkenes or alkynes using sodium sulfinates. The reaction can be performed by a copper-catalyzed oxidation of sodium sulfinates in air. The reaction of alkenes gives (E)-alkenyl sulfones via anti addition of sulfonyl cation and elimination process. Furthermore, the employment of alkynes produces (E) β- haloalkenyl sulfones in the presence of potassium halides. Georg Thieme Verlag Stuttgart · New York.
