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

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

Research output: Contribution to journalArticlepeer-review

9 Scopus 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.

Original languageEnglish
Pages (from-to)13735-13743
Number of pages9
JournalJournal of Organic Chemistry
Volume89
Issue number18
DOIs
StatePublished - 20 Sep 2024

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