Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation

  • Kim, Eunbi
  • Borden, Meredith A.
  • Hwang, Junha
  • Doyle, Abigail G.
  • Dongbang, Sun
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초록

We report a Ni-catalyzed reductive cross-coupling of benzaldehyde-derived acetals with anhydrides or vinyl triflates, enabling modular access to alpha-substituted ethers. Lewis acid/Zn-mediated activation generates alpha-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.

키워드

HALIDESBOND
제목
Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation
저자
Kim, EunbiBorden, Meredith A.Hwang, JunhaDoyle, Abigail G.Dongbang, Sun
DOI
10.1021/acs.orglett.5c02788
발행일
2025-08
유형
Article
저널명
Organic Letters
27
34
페이지
9454 ~ 9459