63735-42-2Relevant academic research and scientific papers
Electrochemical-Induced Hydroxysulfonylation of α-CF3 Alkenes to Access Tertiary β-Hydroxysulfones
Luo, Xu,Wang, Shengchun,Lei, Aiwen
supporting information, p. 1016 - 1022 (2022/02/07)
An electrochemical hydroxysulfonylation of α-CF3 alkenes was accomplished in this work. By using easily available sodium sulfinates as the sulfonylating agents, a series of valuable α-trifluoromethyl tertiary alcohols were synthesized under mild and environmentally friendly electrolysis conditions in moderate to good yields. The preliminary mechanistic investigation indicates that this difunctional reaction involves a radical process via a sulfonyl radical. Gram-scale synthesis shows the significant potential application of this protocol. (Figure presented.).
Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction
Pan, Yi,Wang, Yang,Wang, Yi,Zhang, Feng
supporting information, (2022/02/16)
This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
Access to Sulfoxides under NHC/Photocatalysis via a Radical Pathway
Kuang, Yunyan,Tang, Yulian,Wang, Xuefeng,Wu, Jie,Ye, Shengqing,Zhang, Jun
supporting information, p. 2059 - 2063 (2022/03/31)
A photocatalyzed transformation from sulfinic acids to sulfoxides under visible-light irradiation in the presence of N-heterocyclic carbene is established. Various alkyl groups from four-substituted Hantzsch esters or Meyer nitriles are smoothly converted to the corresponding sulfoxides through a radical coupling pathway in the presence of 1,1-carbonyldiimidazole. This method allows sulfoxide synthesis to refrain from relying on the oxidation of sulfides and provides an alternative route for the preparation of sulfoxides.
Synthesis of β-Keto Sulfones by Oxy-Sulfonylation of Alkynes in HFIP
Chen, Xingyu,Lu, Sixian,Sun, Peng,Wang, Jigang,Yang, Lan,Zheng, Yuyan
supporting information, (2022/03/14)
Herein, we have established a method for the construction of β-keto sulfones through aerobic oxy-sulfonylation of alkynes with sulfinates. The reaction performed employing air as the oxidant and oxygen source. Moreover, this protocol exhibits low consume of sulfinates, short reaction period, and minimal waste. Mechanism study and density functional theory (DFT) calculation showed that the solvent played a significant role in the transformation. (Figure presented.).
Visible-Light-Induced, Palladium-Catalyzed 1,4-Difunctionalization of 1,3-Dienes with Bromodifluoroacetamides
Chen, Kai,Chen, Yi-Xuan,Guan, Jian-Ping,Liu, Zhi-Lin,Xiang, Hao-Yue,Xiao, Jun-An,Xie, Zhen-Zhen,Yang, Hua,Ye, Zhi-Peng,Zheng, Yu
supporting information, p. 924 - 928 (2022/02/05)
A highly modular 1,4-difunctionalization of 1,3-dienes with bromodifluoroacetamides and sulfinates/amines through a photoinduced palladium-catalyzed radical relay process is described herein. This developed protocol offers a facile and general route to ac
Direct C(sp3)–H Sulfonylation of Xanthene Derivatives with Sodium Sulfinates by Oxidative Copper Catalysis
Jiang, Huanfeng,Song, Qinghao,Sun, Yanping,Zhang, Min,Zhao, He
supporting information, p. 371 - 377 (2021/12/24)
By employing a readily available CuCl/DDQ catalyst system, we herein report a direct C(sp3)–H sulfonylation of xanthene derivates with odorless sodium sulfinates. Various 9H-xanthenes, thioxanthenes, and 9,10-dihydroacridines are efficiently transformed into the desired benzylic sulfonyl products via a radical/radical cross-coupling process, proceeding with the merits of broad substrate scope, operational simplicity, good functional group compatibility, and mild reaction conditions.
Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates
Mulina, Olga M.,Ilovaisky, Alexey I.,Opatz, Till,Terent'ev, Alexander O.
supporting information, (2021/01/11)
A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.
Iron-Catalyzed Electrophilic Amination of Sodium Sulfinates with Anthranils
Liang, Baihui,Huang, Junjie,Zhu, Weidong,Li, Yawen,Jiang, Lanping,Gao, Yang,Xie, Feng,Li, Yibiao,Chen, Xiuwen,Zhu, Zhongzhi
, p. 1466 - 1473 (2021/02/09)
A practical method for the synthesis of N-(2-carbonylaryl) benzenesulfonamides via an iron-catalyzed electrophilic amination of sodium sulfinates with anthranils is described. This redox-neutral transformation has high atom efficiency and is achieved under simple and mild reaction conditions. A wide range of anthranils and sodium sulfinates were compatible in this transformation. Moreover, the synthetic potential of this methodology was further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process
Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
supporting information, p. 2152 - 2155 (2021/03/06)
Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.
Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
Lam, Long Yin,Ma, Cong
supporting information, p. 6164 - 6168 (2021/08/16)
A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
