Citation: Kaida Zhou, Jianqiang Chen, Jie Wu. Assembly of 3-sulfonated 2H-pyrrol-2-ones through the insertion of sulfur dioxide with allenoic amides[J]. Chinese Chemical Letters, ;2020, 31(12): 2996-2998. doi: 10.1016/j.cclet.2020.08.037 shu

Assembly of 3-sulfonated 2H-pyrrol-2-ones through the insertion of sulfur dioxide with allenoic amides

Kaida Zhou ^a ,
Jianqiang Chen ^a ,
Jie Wu ^{a, b, *,}

a.
School of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, Taizhou 318000, China
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

jie_wu@fudan.edu.cn

Received Date: 27 July 2020
Revised Date: 6 August 2020
Accepted Date: 24 August 2020
Available Online: 27 August 2020

Figures(3)

Generation of 3-sulfonated 2H-pyrrol-2-ones through a three-component reaction of allenoic amides, sulfur dioxide, and aryldiazonium tetrafluoroborates under metal-free conditions is achieved. This transformation proceeds under mild conditions without the addition of catalysts or additives, giving rise to 3-sulfonated 2H-pyrrol-2-ones in moderate to good yields. Good functional group compatibility is observed. A plausible mechanism is proposed, which is initiated by aryl radicals formed in situ from aryldiazonium tetrafluoroborates and DABCO·(SO₂)₂. Additionally, excellent chemoselectivity and regioselectivity are presented in this transformation.
- Allenoic amide,
- Aryldiazonium tetrafluoroborate,
- 3-Sulfonated 2H-pyrrol-2-one,
- Sulfur dioxide,
- Metal-free
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