Copper Nitrate Mediated Regioselective Difunctionalization of Alkenes with N-Fluorobenzenesulfonimide: A Direct Approach to β-Aminonitrates

Kaijing Zhou; Li Yin; Ying Guo; Chang-Hua Ding; Bin Xu

doi:10.1055/a-1942-7033

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(05): 744-754
DOI: 10.1055/a-1942-7033

paper

Copper Nitrate Mediated Regioselective Difunctionalization of Alkenes with N-Fluorobenzenesulfonimide: A Direct Approach to β-Aminonitrates

Kaijing Zhou

^aDepartment of Chemistry, Affiliated Nantong Hospital of Shanghai University (The Sixth People’s Hospital of Nantong), Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, P. R. of China

,

Li Yin

^aDepartment of Chemistry, Affiliated Nantong Hospital of Shanghai University (The Sixth People’s Hospital of Nantong), Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, P. R. of China

,

Ying Guo

^aDepartment of Chemistry, Affiliated Nantong Hospital of Shanghai University (The Sixth People’s Hospital of Nantong), Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, P. R. of China

,

Chang-Hua Ding∗

^aDepartment of Chemistry, Affiliated Nantong Hospital of Shanghai University (The Sixth People’s Hospital of Nantong), Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, P. R. of China

,

Bin Xu∗

^aDepartment of Chemistry, Affiliated Nantong Hospital of Shanghai University (The Sixth People’s Hospital of Nantong), Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

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Abstract

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Abstract

An efficient copper nitrate mediated difunctionalization of alkenes with N-fluorobenzenesulfonimide (NFSI) has been developed for the direct synthesis of β-aminonitrates in moderate to excellent yields with high regioselectivity. This reaction proceeds through a radical process, where copper nitrate is used as the nitrate source and NFSI as the nitrogen source. The given protocol provides a direct access to functionalized nitrates with operational simplicity, good functional group tolerance, and a wide substrate scope. The reaction can be performed on a gram scale and the synthetic utility of the product is demonstrated.

Key words

copper nitrate - difunctionalization - alkenes - aminonitrates - N-fluorobenzenesulfonimide

Volltext

Referenzen

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