Work

Overcoming limitations in Chan-Lam amination with alkylboronic esters via aminyl radical substitution

Year: 2025

Type: article

Abstract: )-N bonds. Here, we report an N-alkylation protocol that overcomes the limitations of Chan-Lam coupling by using versatile alkylboronic pinacol esters (APEs) as radical precursors via aminyl radical-mediated boron abstraction. This distinct approach enables a versatile N-alkylation applicable to a wide range of APEs and N-nucleophiles with diverse functional groups. Synthetic utility of this protocol is further demonstrated by its ease of scalability, sequential N-alkylation of substrate with multiple reactive sites, and the late-stage modification of several complex bioactive materials.

Source: Nature Communications

DOI: 10.1038/s41467-025-64155-x

Authors: Huanyu Xiao, Panting Cao, Wenhui Xiong, Tao Yang

Institution: Nanchang University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,990

Funder: National Natural Science Foundation of China