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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation
Eunbi Kim1, Meredith A Borden2, Junha Hwang1
1Department of Chemistry, Sogang University, Mapo-gu, Seoul 04107, Republic of Korea.
Abstract:
We report a Ni-catalyzed reductive cross-coupling of benzaldehyde-derived acetals with anhydrides or vinyl triflates, enabling modular access to α-substituted ethers. Lewis acid/Zn-mediated activation generates α-oxy radicals for selective C(sp3)-C(sp2) bond formation via Ni catalysis. This polarity-convergent method unifies ether-variants of benzoin condensation and classical NHK reactions under one reductive platform. Broad scope is demonstrated, and tuning the Lewis acid extends reactivity to dialkyl acetals. Stoichiometric, organometallic, and spectroscopic studies support the reaction mechanism.
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