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

ABSTRACT: Chan-Lam coupling represents one of the most reliable methods for constructing C(sp²)-N bonds under mild conditions. However, application of this technology as a general platform for C(sp³)-N bond assembly remains a longstanding challenge due to the inherent limitation in boron-to-copper transmetalation. In contrast to the conventional two-electron process, the rapid capture of alkyl radicals by copper(II) complex affording the reactive high-valent copper(III) intermediate, has become a key part of the emerging approaches to forge C(sp³)-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

SUBMITTER: Xiao H 

PROVIDER: S-EPMC12521662 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature