A General Platform for Copper-Catalyzed Atom Transfer Radical Addition with Electron-Deficient Olefins
We disclose a broad platform for copper-catalyzed atom transfer radical addition (ATRA) of electron-deficient olefins. Catalytic Cu(dtbbpy)<sub>2</sub>(OTf)<sub>2</sub> enables radical addition of electron-deficient alkyl halides to acrylates, acrylamides, and vinyl sulfones in fair to excellent yields. The resultant ATRA products can be used in a variety of telescoped reactions, including substitution with basic amine nucleophiles to afford α-amino esters. The synthetic utility of the products is further demonstrated through derivatization to give substituted cyclopropanes and a γ,δ-unsaturated ester.
Authors
- Tam D. Ho
- Byung‐Joo Lee (ORCID: https://orcid.org/0000-0001-7091-6688)
- Kami L. Hull (ORCID: https://orcid.org/0000-0003-3102-2686)
- Jacob A. Utley (ORCID: https://orcid.org/0009-0008-7815-9157)
- Hannah C. Wendlandt
Institutions
- The University of Texas at Austin (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-18
- DOI
- https://doi.org/10.1021/acs.orglett.4c04260
- Citations
- 6
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- Welch Foundation
- Eli Lilly and Company
- Novartis
- University of Texas at Austin
- National Institute of General Medical Sciences