Electrochemical Desaturation and β-Thiocyanation of Cyclic Amides

The site-selective functionalization of cyclic amides provides an attractive protocol for the synthesis of valuable molecules. We report herein an electrochemical desaturation and β-thiocyanation of cyclic amides under external oxidant-free conditions. This method exhibits broad functional group tolerance, excellent selectivity, mild reaction conditions and can be applied for late-stage functionalization of bioactive molecules. Mechanistic studies indicate that an enamide intermediate might be involved.

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Publication Details

Journal
Organic Letters
Published
2024-12-19
DOI
https://doi.org/10.1021/acs.orglett.4c04141
Citations
8
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.00

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article

Electrochemical Desaturation and β-Thiocyanation of Cyclic Amides

Li‐Rong Wen, Lin‐Bao Zhang, Weisi Guo, Jin Zhang et al.
8 citations
Organic Letters
Sulfur-Based Synthesis Techniques
2.00
article

Electrochemical Desaturation and β-Thiocyanation of Cyclic Amides

Li‐Rong Wen, Lin‐Bao Zhang, Weisi Guo, Jin Zhang, Kaili Miao, Ming Li, Jiaxin Chen
article en
8 citations

Abstract

The site-selective functionalization of cyclic amides provides an attractive protocol for the synthesis of valuable molecules. We report herein an electrochemical desaturation and β-thiocyanation of cyclic amides under external oxidant-free conditions. This method exhibits broad functional group tolerance, excellent selectivity, mild reaction conditions and can be applied for late-stage functionalization of bioactive molecules. Mechanistic studies indicate that an enamide intermediate might be involved.

Organic LettersVol. 27(1)
Qingdao University of Science and Technology (CN)
Natural Science Foundation of Shandong Province, Science and Technology Support Plan for Youth Innovation of Colleges and Universities of Shandong Province of China
Clean water and sanitation
Openalex Percentile: Top 14%
Sulfur-Based Synthesis Techniques
2.00
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