电子供体-受体络合物激活下亚甲基环丙烷与硫盐的区域选择性磺化反应。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-06-20 Epub Date: 2025-06-06 DOI:10.1021/acs.joc.5c00430

Chao Li, Yinghui Yang, Xianyue Xiong, Xiaoxu Ma, Man Song, Zhengjun He, Hongji Li

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引用次数: 0

摘要

在这里，我们报道了通过电子供体-受体络合物（EDA）激活，亚甲基环丙烷（MCPs）与硫鎓盐的无催化剂磺化反应，使不饱和C = C键和三元环单元具有区域选择性功能化。该可调磺化反应不需要任何光催化剂，并能以中等至较高的收率生成一系列磺化产物。机理实验表明，DABCO和硫铵盐之间形成的电子供体-受体配合物对于SO2的捕获以及MCPs中烯烃和环丙烷单元的后续区域选择性磺化至关重要。

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Regioselective Sulfonylation of Methylenecyclopropanes with Thianthrenium Salts Enabled by Electron Donor-Acceptor Complex Activation.

Herein, we report a catalyst-free sulfonylation of methylenecyclopropanes (MCPs) with thianthrenium salts via electron donor-acceptor complex (EDA) activation, enabling the regioselective functionalization of the unsaturated C═C bond and the three-membered ring unit. The tunable sulfonylation does not require any photocatalysts and generates a series of sulfonyl products in moderate to good yields. Mechanistic experiments indicate that the electron donor-acceptor complexes formed between DABCO and thianthrenium salts are crucial for the trapping of SO₂ as well as the following regioselective sulfonylation of alkene and cyclopropane units of the MCPs.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.