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Photoredox-Catalyzed Metal-free Regio- & Stereoselective C(sp2)-H Amination of Enamides with N-aminopyridium salts
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  • Zheng-Bao Qin,
  • Kun Ni,
  • Li Wang,
  • Xiao-Di Wu,
  • Yu Zhang,
  • Kai Zhao
Zheng-Bao Qin
Nanjing Tech University
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Kun Ni
Nanjing Tech University
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Li Wang
Nanjing Tech University
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Xiao-Di Wu
Nanjing Tech University
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Yu Zhang
Nanjing Tech University
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Kai Zhao
Nanjing Tech University

Corresponding Author:ias_kzhao@njtech.edu.cn

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Abstract

A visible-light-induced photoredox-catalyzed regioselective and stereoselective C(sp2)-H amination of enamides with bench-stable and easily accessible N-aminopyridium salts is developed, affording synthetically and biologically prominent vicinal 1,2-diamine scaffolds in broad substrate scope and excellent functional group compatibility. The transformation proceeded through a radical pathway involving the Giese addition of the relatively electrophilic N-centered amidyl radical species to nucleophilic β-olefinic position of enamides followed by the ensuing single electron oxidation and β-H elimination, delivering geometrically-defined Z-configured β-amino enamides. The operational simplicity, environmentally friendliness and cost efficiency of this methodology has paved a new avenue to enrich the arsenal of synthetically crucial functionalized enamides and their derivatives.
31 Mar 2024Submitted to Chinese Journal of Chemistry
03 Apr 2024Submission Checks Completed
03 Apr 2024Assigned to Editor
03 Apr 2024Review(s) Completed, Editorial Evaluation Pending
09 Apr 2024Reviewer(s) Assigned
12 Apr 2024Editorial Decision: Revise Minor