Issue 21, 2023

Rhodium-catalyzed electrochemical [2 + 2 + 2] cyclotrimerization of 1,3-butadiynes toward hexasubstituted arenes

Abstract

Electrochemical transition metal catalysis has been regarded as a synthetically attractive method for the construction of diverse organic frameworks because it obviates the use of chemical redox reagents. Herein, we report an elegant rhodium-catalyzed electrochemical [2 + 2 + 2] cyclotrimerization of 1,3-butadiynes for the regioselective synthesis of structurally diverse hexasubstituted arenes in an undivided cell. This methodology features excellent regioselectivity, good functional group tolerance, and high atom economy. Mechanistic studies show that the formation of five-membered C–Rh metallacycle species is crucial, and it would sequentially undergo consecutive coordination, migratory insertion and reductive elimination to deliver the desired arenes.

Graphical abstract: Rhodium-catalyzed electrochemical [2 + 2 + 2] cyclotrimerization of 1,3-butadiynes toward hexasubstituted arenes

Supplementary files

Article information

Article type
Paper
Submitted
31 7 2023
Accepted
20 9 2023
First published
26 9 2023

Green Chem., 2023,25, 8858-8862

Rhodium-catalyzed electrochemical [2 + 2 + 2] cyclotrimerization of 1,3-butadiynes toward hexasubstituted arenes

M. Luo, G. Lv, J. Qin, C. Xu, Y. Li and J. Li, Green Chem., 2023, 25, 8858 DOI: 10.1039/D3GC02831C

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