Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C–O Activation
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(sp<sup>3</sup>)-C(sp<sup>2</sup>) 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.
Authors
- Sun Dongbang (ORCID: https://orcid.org/0000-0001-6599-3603)
- Junha Hwang
- Eun‐Bi Kim (ORCID: https://orcid.org/0000-0002-1980-0636)
- Abigail G. Doyle (ORCID: https://orcid.org/0000-0002-6641-0833)
- Meredith A. Borden (ORCID: https://orcid.org/0000-0001-5369-8199)
Institutions
- Sogang University (KR)
- University of California, Los Angeles (US)
- Princeton University (US)
- University of California System (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-18
- DOI
- https://doi.org/10.1021/acs.orglett.5c02788
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Research Foundation of Korea
- National Institute of General Medical Sciences