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 جوٗلایی 2023
Accepted
20 ستمبر 2023
First published
26 ستمبر 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements