Palladium-Catalyzed Regiodivergent Three Component Alkenylamination of Terminal Dienes with Alkyl and Aryl Amines

08 September 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We report a palladium-catalyzed method for 4,3- or 4,1-selective alkenylamination of terminal dienes. Three component couplings proceed with alkenyl triflates and several amines, giving vicinal carboamination with a Xantphos-supported catalyst and distal difunctionalization with a phosphoramidite ligand. Experimental evidence indicates selectivity in the former reactions is largely influenced by the substrate whereas the latter is catalyst controlled, orchestrated by a key pi-stacking interaction among the ligand, solvent, and substrate.

Keywords

diene
alkyl amine
palladium
regiodivergent
three component coupling

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.