28995-75-7Relevant articles and documents
Solvent-Driven Mono- and Bis-sulfenylation of (E)-β-Iodovinyl Sulfones with Thiols for Flexible Synthesis of 1,2-Thiosulfonylalkenes and 1,2-Dithioalkenes
Krishna, Gamidi Rama,Kumari, Arram Haritha,Reddy, Raju Jannapu,Sharadha, Nunavath
supporting information, (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.
Electrochemical Induced Regio- and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)-β-Iodovinyl Sulfones
Zhang, Xinghua,Lu, Danna,Wang, Zhenwei
supporting information, p. 4284 - 4287 (2021/06/16)
An efficient, green, and oxidant-free electrochemical method for alkyne difunctionalization was described. Using undivided electrochemical cell for iodosulfonylation of alkynes with commercially available iodide radical (NaI), arylsulfonyl radical (ArSOs
Unprecedented Reactivity of β-Iodovinyl Sulfones: An Efficient Synthesis of β-Keto Sulfones and β-Keto Thiosulfones
Reddy, Raju Jannapu,Kumar, Jangam Jagadesh,Kumari, Arram Haritha
supporting information, p. 3771 - 3775 (2019/06/24)
An unprecedented reactivity of (E)-β-iodovinyl sulfones in the presence of NaOAc is reported. The (E)-β-iodovinyl sulfones were treated with NaOAc in DMSO/H2O to yield β-keto sulfones in moderate to high yields. A novel oxidative difunctionalization of β-iodovinyl sulfones with thiosulfonates and NaOAc in DMF has been developed. This metal-free oxosulfenylation is an operationally simple to access a wide range of β-keto thiosulfones (α-thioaryl-β-keto sulfones) in moderate to high yields. The transformations were reliable at gram-scale, thus illustrating its efficiency and practicality. A plausible mechanism for the protocol is also proposed.