Citation: Min Yang, Huiqi Han, Hui Jiang, Shengqing Ye, Xiaona Fan, Jie Wu. Photoinduced reaction of potassium alkyltrifluoroborates, sulfur dioxide and para-quinone methides via radical 1, 6-addition[J]. Chinese Chemical Letters, ;2021, 32(11): 3535-3538. doi: 10.1016/j.cclet.2021.05.007 shu

Photoinduced reaction of potassium alkyltrifluoroborates, sulfur dioxide and para-quinone methides via radical 1, 6-addition

Min Yang ^a ,
Huiqi Han ^a ,
Hui Jiang ^b ,
Shengqing Ye ^{b, *,} ,
Xiaona Fan ^{a, *,} ,
Jie Wu ^{b, c, d, *,}

a.
Department of Forensic Science, Collaborative Innovation Center for Gannan Oil-tea Camellia Industrial Development, Gannan Medical University, Ganzhou 341000, China
b.
School of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou 318000, China
c.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
d.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

ysq0607@gmail.com

fxn918@126.com

jie_wu@fudan.edu.cn

Received Date: 26 March 2021
Revised Date: 7 May 2021
Accepted Date: 8 May 2021
Available Online: 15 May 2021

Figures(3)

A photoinduced reaction of potassium alkyltrifluoroborates, sulfur dioxide, and para-quinone methides under visible light irradiation at room temperature is developed, giving rise to diarylmethyl alkylsulfones in moderate to good yields. This reaction works well under photocatalysis with a broad substrate scope by using DABCO·(SO₂)₂ as the source of sulfur dioxide. Mechanistic study shows that this transformation is initiated by alkyl radicals generated in situ from potassium alkyltrifluoroborates in the presence of photocatalyst. The subsequent insertion of sulfur dioxide and radical 1, 6-addition of para-quinone methides with alkylsulfonyl radical intermediates afford the corresponding diarylmethyl alkylsulfones.
- Potassium alkyltrifluoroborate,
- para-Quinone methide,
- Sulfur dioxide,
- Radical 1, 6-addition,
- Visible light irradiation
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