Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C–O Bond Cleavage

With the assistance of nickel as catalyst, 2,2'-bipyridine (bpy) as ligand, and manganese as reducing metal, the reductive amidation of isocyanates with readily accessible aryl fluorosulfates could be successfully accomplished. The reactions proceeded effectively via C-O bond activation in DMF at room temperature, enabling the facile synthesis of a range of structurally diverse amides in moderate to high yields with broad functionality compatibility. In addition, the synthetic usefulness of the method was further demonstrated by applying the reaction in scale-up synthesis and the late-stage functionalization of complex molecules with biological activities.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-30
DOI
https://doi.org/10.1021/acs.joc.4c01399
Citations
16
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
3.74

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article

Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C–O Bond Cleavage

Li-Xin Zhai, Weidong Rao, Xue‐Qiang Chu, Zhi‐Liang Shen et al.
16 citations
The Journal of Organic Chemistry
Chemical Synthesis and Analysis
3.74
article

Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C–O Bond Cleavage

Li-Xin Zhai, Weidong Rao, Xue‐Qiang Chu, Zhi‐Liang Shen, Chengping Miao, Gan‐Qi Qin, Xu-Rong Cao, Xiaocong Zhou, Jiao Wang
article en
16 citations

Abstract

With the assistance of nickel as catalyst, 2,2'-bipyridine (bpy) as ligand, and manganese as reducing metal, the reductive amidation of isocyanates with readily accessible aryl fluorosulfates could be successfully accomplished. The reactions proceeded effectively via C-O bond activation in DMF at room temperature, enabling the facile synthesis of a range of structurally diverse amides in moderate to high yields with broad functionality compatibility. In addition, the synthetic usefulness of the method was further demonstrated by applying the reaction in scale-up synthesis and the late-stage functionalization of complex molecules with biological activities.

The Journal of Organic ChemistryVol. 89(18)
Nanjing Tech University (CN), Nanjing Forestry University (CN), Jiaxing University (CN)
Nanjing Tech University
Openalex Percentile: Top 6%
Chemical Synthesis and Analysis
3.74
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