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

Yin-Ling LiuJian LiuXin-Yu LiPeng HeYu-Xuan LiuMei XiangShi Tang
Published in: Chemical communications (Cambridge, England) (2024)
A radical 1,4-aryl migration enabling a cross-electrophile coupling reaction toward remote trans alkylation 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.
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