Carbon Diarylation of Iodonium Ylides for Construction of All-Carbon Quaternary Centers

28 March 2025, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The construction of all-carbon quaternary centers via multiple bond formations remains a significant challenge in synthetic chemistry. Herein, we report a tandem diarylation process initiated via [2+2] cycloaddition between aryne species and iodonium ylides to form 4-membered iodocyclobutane intermediate. This intermediate subsequently undergoes a 1,2-aryl migration from iodonium to carbon, producing unsymmetrical a-diarylated malonic esters. The process is remarkable for its mild conditions, broad substrate compatibility, and the capability to form two C−C bonds and one C-I bond in a single step. This work also uncovers a novel reaction mode for iodonium ylide reagents.

Supplementary materials

Title
Description
Actions
Title
Carbon Diarylation of Iodonium Ylides for Construction of All-Carbon Quaternary Centers
Description
Experimental procedures, analytical data, and copies of 1H and 13C NMR spectra of all newly synthesized compounds
Actions

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.