Work

A General Platform for Copper-Catalyzed Atom Transfer Radical Addition with Electron-Deficient Olefins

Year: 2024

Type: article

Abstract: We disclose a broad platform for copper-catalyzed atom transfer radical addition (ATRA) of electron-deficient olefins. Catalytic Cu(dtbbpy) 2 (OTf) 2 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c04260

Authors: Hannah C. Wendlandt, Jacob A. Utley, Byung Joo Lee, Tam D. Ho, Kami L. Hull

Institution: The University of Texas at Austin

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green