Nickel-Catalyzed\nReductive Amidation of Aryl Fluorosulfates\nwith Isocyanates: Synthesis of Amides via C–O Bond Cleavage

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

Publication Details

Journal
Figshare
Published
2024-08-30
DOI
https://doi.org/10.1021/acs.joc.4c01399.s001
Primary Topic
Chemical Synthesis and Analysis
Type
article
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article

Nickel-Catalyzed\nReductive Amidation of Aryl Fluorosulfates\nwith Isocyanates: Synthesis of Amides via C–O Bond Cleavage

Figshare
Chemical Synthesis and Analysis
article

Nickel-Catalyzed\nReductive Amidation of Aryl Fluorosulfates\nwith Isocyanates: Synthesis of Amides via C–O Bond Cleavage

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Abstract

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

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Chemical Synthesis and Analysis
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Nickel-Catalyzed\nReductive Amidation of Aryl Fluorosulfates\nwith Isocyanates: Synthesis of Amides via C–O Bond Cleavage · Figshare (2024) | TGRS Research Map | TGRS