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

Authors :
Qin GQ
Wang J
Cao XR
Chu XQ
Zhou X
Rao W
Zhai LX
Miao C
Shen ZL
Source :
The Journal of organic chemistry [J Org Chem] 2024 Aug 30. Date of Electronic Publication: 2024 Aug 30.
Publication Year :
2024
Publisher :
Ahead of Print

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.

Details

Language :
English
ISSN :
1520-6904
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
39213645
Full Text :
https://doi.org/10.1021/acs.joc.4c01399