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Updated: May 22, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Nickel-Catalyzed Reductive 1,4-Alkylacylation of 1,3-Enynes Enabling Synthesis of Allenyl Ketones
Quanyuan Wang1, Keyi Peng1, Xiangyuan Yao1
1Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Hunan, Xiangtan 411105, China.
Abstract:
A nickel-catalyzed reductive 1,4-alkylacylation of 1,3-enynes has been established using nonactivated tertiary alkyl bromides and aromatic anhydrides as dual electrophiles. This protocol enables efficient assembly of tetrasubstituted allenyl ketones with high chemo- and regioselectivity. Mechanistic insights reveal the radical relay process involving the synergistic interactions of nickel and zinc. The allenyl ketone products serve as modular building blocks, particularly for constructing fully carbon-substituted furans via Au-catalyzed cycloisomerization with selective 1,2-aryl migration, enhancing the synthetic practicality.
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