A Domino Radical Amidation/Semipinacol Approach to All-Carbon Quaternary Centers Bearing an Aminomethyl Group

Dhak, Mandeep S.; Arunprasath, Dhanarajan; Argent, Stephen P.; Cuthbertson, James David

Abstract

A photoredox-mediated radical amidation ring-expansion sequence that enables the generation of all-carbon quaternary centers bearing a protected aminomethyl substituent is described. The methodology can be applied to both styrene and unactivated alkene substrates generating structurally diverse sp3-rich amine derivatives in a concise manner.

• Journal Article Type: Article
• Acceptance Date: Jun 2, 2023
• Online Publication Date: Jul 24, 2023
• Publication Date: Aug 21, 2023
• Deposit Date: Jun 28, 2023
• Publicly Available Date: Jul 25, 2024
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 29
• Issue: 47
• Article Number: e202300922
• DOI: https://doi.org/10.1002/chem.202300922
• Keywords: Aminofunctionalisation, ring expansion, nitrogen-centred radicals, Photoredox catalysis, semipinacol rearrangement
• Public URL: https://nottingham-repository.worktribe.com/output/22172826
• Publisher URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202300922