Visible light-promoted copper catalyzed regioselective acetamidation of terminal alkynes by arylamines

Herein, we describe a copper photoredox catalyzed synthesis of acetamide via regioselective C-N coupling of arylamines with terminal alkynes using molecular oxygen (O 2 ) as an oxidant at room temperature under visible light irradiation (47 examples). Unique simultaneous formation of both amide and...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2020-02, Vol.22 (4), p.1164-117
Main Authors: Pampana, V. Kishore Kumar, Sagadevan, Arunachalam, Ragupathi, Ayyakkannu, Hwang, Kuo Chu
Format: Article
Language:English
Subjects:
Alkynes
Amines
Biological activity
Catalysts
Chemical synthesis
Copper
Coupling (molecular)
Crystallography
Green chemistry
Inhibitors
Irradiation
Labeling
Light irradiation
Organic compounds
Oxidants
Oxidizing agents
Oxygen
Phosphodiesterase
Radiation
Reagents
Regioselectivity
Room temperature
Substrates
β-Site APP-cleaving enzyme 1
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Summary:Herein, we describe a copper photoredox catalyzed synthesis of acetamide via regioselective C-N coupling of arylamines with terminal alkynes using molecular oxygen (O 2 ) as an oxidant at room temperature under visible light irradiation (47 examples). Unique simultaneous formation of both amide and ester functionalities occurs via intramolecular cyclization in a single-step reaction in the case of anthranilic acids using inexpensive copper as a catalyst and eco-friendly O 2 as an oxidant and reagent. Different substrates undergo different reaction pathways to generate similar acetamide products, as evidenced by 18 O 2 labelling experiments. The current protocol was also applied for the rapid, few step preparation of biologically active inhibitors (BACE-1 and PDE4). This process can be readily scaled up to a gram scale, and calculations of green metrics suggest the economic feasibility and eco-friendly nature of the current photoredox approach. Herein, we describe a copper photoredox catalyzed synthesis of acetamide via regioselective C-N coupling of arylamines with terminal alkynes using molecular oxygen (O 2 ) as an oxidant at room temperature under visible light irradiation (47 examples).
ISSN:1463-9262
1463-9270
DOI:10.1039/c9gc03608c