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Zhou K, Liu JB, Xie W, et al. Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation. Chem Commun (Camb). 2020;56(17):2554-2557doi: 10.1039/d0cc00351d.
Zhou, K., Liu, J. B., Xie, W., Ye, S., & Wu, J. (2020). Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation. Chemical communications (Cambridge, England), 56(17), 2554-2557. https://doi.org/10.1039/d0cc00351d
Zhou, Kaida, et al. "Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation." Chemical communications (Cambridge, England) vol. 56,17 (2020): 2554-2557. doi: https://doi.org/10.1039/d0cc00351d
Zhou K, Liu JB, Xie W, Ye S, Wu J. Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation. Chem Commun (Camb). 2020 Feb 27;56(17):2554-2557. doi: 10.1039/d0cc00351d. PMID: 32010913.
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Chem Commun (Camb). 2020 Feb 27;56(17):2554-2557. doi: 10.1039/d0cc00351d.

Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation.

Chemical communications (Cambridge, England)

Kaida Zhou, Jin-Biao Liu, Wenlin Xie, Shengqing Ye, Jie Wu

Affiliations

  1. School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China. [email protected] [email protected].
  2. School of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, Ganzhou 341000, China.
  3. School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
  4. School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China. [email protected] [email protected] and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

PMID: 32010913 DOI: 10.1039/d0cc00351d

Abstract

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.

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