Issue 32, 2024

A radical 1,4-aryl migration enables nickel-catalysed remote cross-electrophile coupling of β-bromo amino acid esters with vinyl triflates

Abstract

A radical 1,4-aryl migration enabling a cross-electrophile coupling reaction toward remote transalkylation of N-benzyl alanine has been developed. In this strategy, with the occurrence of a radical-mediated Turce-Smiles rearrangement, key α-aminoalkyl radicals are generated. The as-formed α-aminoalkyl radical serves as a robust coupling partner for cross-electrophilic coupling with vinyl triflates, affording a series of olefin-tethered amino acid motifs.

Graphical abstract: A radical 1,4-aryl migration enables nickel-catalysed remote cross-electrophile coupling of β-bromo amino acid esters with vinyl triflates

Supplementary files

Article information

Article type
Communication
Submitted
07 Feb 2024
Accepted
14 Mar 2024
First published
15 Mar 2024

Chem. Commun., 2024,60, 4306-4309

A radical 1,4-aryl migration enables nickel-catalysed remote cross-electrophile coupling of β-bromo amino acid esters with vinyl triflates

Y. Liu, J. Liu, X. Li, P. He, Y. Liu, M. Xiang and S. Tang, Chem. Commun., 2024, 60, 4306 DOI: 10.1039/D4CC00627E

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