1384586-07-5Relevant academic research and scientific papers
Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation
Zhou, Kaida,Liu, Jin-Biao,Xie, Wenlin,Ye, Shengqing,Wu, Jie
supporting information, p. 2554 - 2557 (2020/03/10)
Metal-free insertion of sulfur dioxide with aryl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-(arylsulfonyl)acetonitriles in moderate to good yields. Alkyl iodide is also workable under these conditions. This transformation proceeds smoothly under mild conditions with a broad substrate scope. Various functional groups are compatible including amino, ester, halo, and trifluoromethyl groups. No metal catalyst or additive is needed during the reaction process. Mechanistic studies show that under ultraviolet irradiation, an aryl radical is generated in situ from aryl iodide, which undergoes subsequent sulfonylation via the insertion of sulfur dioxide leading to arylsulfonyl radical intermediates. Then the arylsulfonyl radical reacts with 3-azido-2-methylbut-3-en-2-ol giving rise to the corresponding 2-(arylsulfonyl)acetonitrile.
Use of (Z)-β-(2-fluorobenzenesulfonyl)vinylamines as novel synthons in the synthesis of 1,4-benzothiazine derivatives
Tsui, Gavinchit,Singjunla, Yuttapong,Lautens, Mark
, p. 1359 - 1364 (2012/06/30)
A novel synthetic route for arylated 1,4-benzothiazine derivatives has been developed. This method utilizes a key intramolecular nucleophilic aromatic substitution step of the corresponding (Z) - (2-fluorobenzenesulfonyl)vinylamine intermediate to construct the benzothiazine ring. A wide range of aryl and heteroaryl substituent groups can be installed from commercial boronic acids. Both mono- and diarylated products have been synthesized in good yields and with good functional group tolerance. Georg Thieme Verlag Stuttgart · New York.
