Visible Light-Mediated [2+2]-Cycloadditions for the Formation of Macrocyclic Dimers

21 October 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Macrocyclic, dimeric lactones have known pharmacological activities that make them attractive synthetic targets but are typically synthesized following an iterative approach. Herein, we report a visible light-mediated approach to macrocyclic dimers that allows access to 1- and 2-azetine-containing dimeric lactones. Notably, up to 30-membered macrocycles are formed following this strategy that results in 1-azetine dimers via four consecutive triplet energy transfers, while 2-azetines are formed in a sequence relying on two consecutive triplet energy transfers. Computational investigations provide important insights into the reaction mechanism, suggesting that intermolecular [2+2]-cycloadditions are preferred under non-standard Curtin-Hammett conditions over the corresponding intramolecular reaction.




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.