<i>t</i>-BuOK-Induced, NH<sub>3</sub>·MeOH-Promoted Electrochemical C(sp<sup>3</sup>)–H Amination of Saturated Heterocycles with Sulfoximines

The <i>t</i>-BuOK-induced electrochemical C(sp<sup>3</sup>)-H amination of saturated heterocycles with sulfoximines was reported. <i>t</i>-BuOK rather than dangerous peroxides was used as the precursor of the <i>tert</i>-butoxy radical, which was induced by electrochemistry; this process has not been previously reported. Notably, we found that NH<sub>3</sub>·MeOH can serve as a promoter in electrochemical oxidation reactions. This C-H/N-H cross-dehydrogenation coupling reaction produces only the green byproduct H<sub>2</sub> and has the advantages of atom economy, lack of transition metals, lack of external oxidants, and mild reaction conditions.

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Publication Details

Journal
Organic Letters
Published
2025-07-14
DOI
https://doi.org/10.1021/acs.orglett.5c02042
Citations
4
Primary Topic
Synthesis and Catalytic Reactions
Type
article
Field-Weighted Citation Impact
3.74
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article

t-BuOK-Induced, NH3·MeOH-Promoted Electrochemical C(sp3)–H Amination of Saturated Heterocycles with Sulfoximines

Hui Gao, Peng-Zhan Zhang, Pei-Long Wang, Zuopeng Xu et al.
4 citations
Organic Letters
Synthesis and Catalytic Reactions
3.74
article

t-BuOK-Induced, NH3·MeOH-Promoted Electrochemical C(sp3)–H Amination of Saturated Heterocycles with Sulfoximines

Hui Gao, Peng-Zhan Zhang, Pei-Long Wang, Zuopeng Xu, Qing‐Ru Zhu
article en
4 citations

Abstract

The <i>t</i>-BuOK-induced electrochemical C(sp<sup>3</sup>)-H amination of saturated heterocycles with sulfoximines was reported. <i>t</i>-BuOK rather than dangerous peroxides was used as the precursor of the <i>tert</i>-butoxy radical, which was induced by electrochemistry; this process has not been previously reported. Notably, we found that NH<sub>3</sub>·MeOH can serve as a promoter in electrochemical oxidation reactions. This C-H/N-H cross-dehydrogenation coupling reaction produces only the green byproduct H<sub>2</sub> and has the advantages of atom economy, lack of transition metals, lack of external oxidants, and mild reaction conditions.

Organic LettersVol. 27(29)
Ministry of Education of the People's Republic of China (CN), Huaibei Normal University (CN)
Clean water and sanitation
Openalex Percentile: Top 7%
Synthesis and Catalytic Reactions
3.74
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<i>t</i>-BuOK-Induced, NH<sub>3</sub>·MeOH-Promoted Electrochemical C(sp<sup>3</sup>)–H Amination of Saturated Heterocycles with Sulfoximines — Hui Gao, Peng-Zhan Zhang, et al. · Organic Letters (2025) | TGRS Research Map | TGRS