16212-08-1Relevant academic research and scientific papers
PHOTODECOMPOSITION OF SELENOSULFONATES AND THEIR FACILE PHOTOADDITION TO ALKENES1
Gancarz, Roman A.,Kice, John L.
, p. 4155 - 4158 (1980)
Phenyl areneselenosulfonates (1) are very photosensitive and easily undergo photodecomposition via initial homolysis of the Se-S bond.In the presence alkenes this facile photodissociation of 1 can be used to initiate a free radical chain reaction (eq 6) that leads to addition of 1 to the alkene to form β-phenylselenosulfones (2).The photoaddition requires much shorter reaction times than the non-photolytic addition of 1 to alkenes described recently.
Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature
Bao, Wen-Hui,Ying, Wei-Wei,Xu, Xu-Dong,Zhou, Guo-Dong,Meng, Xiao-Xiao,Wei, Wen-Ting,Liu, Yan-Yun,Li, Qiang
, p. 55 - 58 (2019)
Herein, metal-free radical Heck-type reaction of styrenes with sulfonyl hydrazides to synthesize vinyl sulfones is developed. The reaction is performed under economical TBAI/TBHP system on water in open air at room temperature, which proceeds through the
Alkyne-based, highly stereo- and regioselective synthesis of stereodefined functionalized vinyl tellurides
Huang,Liang,Xu,He
, p. 74 - 80 (2001)
(Z)-β-Aryltellurovinylphosphonates and (Z)-β-aryltellurovinyl sulfones were synthesized via the highly stereoselective anti-hydrotelluration of 1-alkynylphosphonates and 1-alkynyl sulfones. The configurations of these compounds were characterized via sup
Photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls: Facile access to substituted dihydropyrazoles
Yu, Jing-Miao,Lu, Guo-Ping,Cai, Chun
, p. 5342 - 5345 (2017)
A mild and efficient method for the photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls has been described. This strategy provides a potential protocol for the construction of functionalized 4,5-dihydropyrazoles in moderate to high yields.
One-pot approach for the regioselective synthesis of β-keto sulfones based on acid-catalyzed reaction of sulfonyl chlorides with arylacetylenes and water
Lai, Chunbo,Xi, Chanjuan,Jiang, Yanfeng,Hua, Ruimao
, p. 513 - 515 (2005)
Reaction of sulfonyl chlorides with arylacetylenes and water in the presence of a catalytic amount of sulfonic acid in THF provided β-keto sulfones in good yields with excellent regioselectivity.
Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
Ojha, Subhadra,Panda, Niranjan
supporting information, p. 1292 - 1298 (2022/02/19)
A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
The Sulfinylsulfonation of alkynes for β-Sulfinyl alkenylsulfone
Feng, Chengjie,Ning, Yongquan,Song, Qingmin,Wang, Zikun,Wu, Yong,Zhang, Zhansong,Zhao, Wanjun
supporting information, (2022/05/23)
Here we report the sulfinylsulfonation of alkynes to afford β-sulfinyl alkenylsulfone products with a broad substrate scope, excellent functional group compatibility, and high yield. Moreover, the sulfinylsulfonation reaction of enyne can also be realized for constructing functionalized carbo- and heterocycles through a radical cascade cyclization process.
Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature
Jiang, Hezhong,Li, Jiahong,Li, Jun-Long,Lin, Li,Liu, Jianchen,Liu, Xiang-Wei,Wang, Jingxia,Yang, Zhonglie,Zhang, Xiaobin,Zheng, Jiale
supporting information, p. 5467 - 5473 (2021/08/16)
A green and efficient visible-light-induced iodosulfonyl reaction of alkenes in water using an EDA complex strategy at room temperature has been disclosed. The addition of a cationic surfactant allows for the easy formation of colored EDA complexes in water. The hydrophobic effect of the core in the surfactant aggregates, which act as a reaction medium formed by the surfactants themselves in water, plays a significant role in stabilizing the transition state and decreasing the activation energy of the reaction. Remarkably, transition-metal catalysts and organic solvents were not required in this transformation. Moreover, it displayed a broad substrate scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of β-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.
Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis
Cui, Wenwen,Jiang, Min,Lv, Jian,Song, Xiuyan,Sun, Kai,Xu, Guiyun,Yan, Qiuli,Yang, Daoshan
, p. 3663 - 3668 (2021/05/31)
An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.
Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants
Jeremias, Noah,Mohr, Lisa-Marie,Bach, Thorsten
supporting information, p. 5674 - 5678 (2021/08/03)
2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).
