Umpolung Approach for the α-Alkylation of Benzylic Amines Enabled by Superelectron Donors.

Authors

Wenjuan Xiao, Wen Liu, Xi Chen, Changping Fang, Mengtao Ma, Binlin Zhao

Published in

Organic letters. Sep 11, 2025. Epub Sep 11, 2025.

Abstract

Herein we describe a general transition-metal-free umpolung protocol for the synthesis of α-alkylated benzylic amines. By employing two distinct classes of ketimines and easily available alkyl thianthrenium salts as substrates, this method provides a flexible and straightforward approach to access structurally diverse α-alkylated benzylic amines under mild reaction conditions with high efficiency. Furthermore, this methodology could be extended to the regioselective alkylation of allylic amines and a-amino acid derivatives. Mechanistic investigations suggest that the deprotonated ketimines act as super electron donors (SEDs), engaging in intermolecular single-electron transfer (SET) with alkyl thianthrenium salts to generate key radical intermediates, which play a pivotal role in the base-promoted reaction pathway.

PMID:
40934470
Bibliographic data and abstract were imported from PubMed on 12 Sep 2025.

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