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

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Abstract

Herein, we describe a copper photoredox catalyzed synthesis of acetamide via regioselective C–N coupling of arylamines with terminal alkynes using molecular oxygen (O2) 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 O2 as an oxidant and reagent. Different substrates undergo different reaction pathways to generate similar acetamide products, as evidenced by 18O2 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.

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

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Publication details

The article was received on 20 Oct 2019, accepted on 19 Nov 2019 and first published on 21 Nov 2019


Article type: Paper
DOI: 10.1039/C9GC03608C
Green Chem., 2020, Advance Article

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

    V. K. K. Pampana, A. Sagadevan, A. Ragupathi and K. C. Hwang, Green Chem., 2020, Advance Article , DOI: 10.1039/C9GC03608C

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