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Photoinduced Palladium-Catalyzed 1,2-Aminoalkylation of Aromatic Alkenes with Hydroxyl as the Directing Group.

Jing YangChen-Rui LiXu GuoZhuo ChenXuan ChenLi-Xin Li
Published in: Organic letters (2024)
The hybrid nature of Pd(I)-alkyl radical species has enabled a wide array of radical-based transformations. However, in this transformation, the secondary Pd(I)-alkyl radical species are prone to recombining into Pd(II)-alkyl species to give Heck-type products via β-H loss. Herein, we report a visible-light-induced, three-component Pd-catalyzed 1,2-aminoalkylation of alkenes with readily available alkyl halides and amines to construct C-C and C-N bonds simultaneously. Mechanistic investigation shows that the intermediate of o -quinone methide produced is the key factor in the transformation.
Keyphrases
  • ionic liquid
  • high resolution
  • mass spectrometry
  • high density