Issue 22, 2022

Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu(i) complexes under visible light

Abstract

Herein, we report a substituent-controlled synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu(I) complexes under visible-light irradiation. The in situ generated α-stilbene radical Cu(II)-complex was achieved by photoinduced Csp–Csp2 coupling of copper(I) acetylides and aryl radicals catalysed by heteroleptic Cu(I) complexes. This photochemical approach offered high atom economy with a low E-factor and functional group tolerance under mild reaction conditions. Mechanistic insights clearly show that the reaction proceeded via copper(I) acetylides and the phenyl radical intermediate pathway.

Graphical abstract: Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu(i) complexes under visible light

Supplementary files

Article information

Article type
Communication
Submitted
12 Aug 2022
Accepted
19 Oct 2022
First published
20 Oct 2022

Green Chem., 2022,24, 8685-8690

Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu(I) complexes under visible light

N. Neerathilingam, K. Prasanth and R. Anandhan, Green Chem., 2022, 24, 8685 DOI: 10.1039/D2GC03011J

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