Issue 11, 2024

Palladium-catalyzed and ligand-controlled divergent cycloadditions of vinylidenecyclopropane-diesters with para-quinone methides enabled by zwitterionic π-propargyl palladium species

Abstract

A palladium-catalyzed divergent synthesis of spiro-cyclohexadienones with a five- or a six-membered ring by a cycloaddition reaction of vinylidenecyclopropane-diesters (VDCP-diesters) with p-quinone methides (p-QMs) was disclosed. This protocol features a switchable process between [3 + 2] and [4 + 2] cycloadditions tuned by subtle choice of the phosphine ligand. The substrate scopes have been investigated and the reaction mechanism has been clarified by mechanistic studies; and DFT calculations also revealed that the coordination modes of the ligands with the substrates and the bite angle of the ligands play critical roles in the product regioselectivity.

Graphical abstract: Palladium-catalyzed and ligand-controlled divergent cycloadditions of vinylidenecyclopropane-diesters with para-quinone methides enabled by zwitterionic π-propargyl palladium species

Supplementary files

Article information

Article type
Research Article
Submitted
27 Feb 2024
Accepted
14 Apr 2024
First published
16 Apr 2024

Org. Chem. Front., 2024,11, 3214-3224

Palladium-catalyzed and ligand-controlled divergent cycloadditions of vinylidenecyclopropane-diesters with para-quinone methides enabled by zwitterionic π-propargyl palladium species

J. Shen, Y. Long, M. Shi and Y. Wei, Org. Chem. Front., 2024, 11, 3214 DOI: 10.1039/D4QO00368C

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