A General Platform\nfor Copper-Catalyzed Atom Transfer\nRadical Addition with Electron-Deficient Olefins

We\ndisclose a broad platform for copper-catalyzed atom transfer\nradical addition (ATRA) of electron-deficient olefins. Catalytic Cu(dtbbpy)<sub>2</sub>(OTf)<sub>2</sub> enables radical addition of electron-deficient\nalkyl halides to acrylates, acrylamides, and vinyl sulfones in fair\nto excellent yields. The resultant ATRA products can be used in a\nvariety of telescoped reactions, including substitution with basic\namine nucleophiles to afford α-amino esters. The synthetic utility\nof the products is further demonstrated through derivatization to\ngive substituted cyclopropanes and a γ,δ-unsaturated ester.

Publication Details

Journal
Figshare
Published
2024-12-18
DOI
https://doi.org/10.1021/acs.orglett.4c04260.s002
Primary Topic
Genetic diversity and population structure
Type
article
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article

A General Platform\nfor Copper-Catalyzed Atom Transfer\nRadical Addition with Electron-Deficient Olefins

Figshare
Genetic diversity and population structure
article

A General Platform\nfor Copper-Catalyzed Atom Transfer\nRadical Addition with Electron-Deficient Olefins

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Abstract

We\ndisclose a broad platform for copper-catalyzed atom transfer\nradical addition (ATRA) of electron-deficient olefins. Catalytic Cu(dtbbpy)<sub>2</sub>(OTf)<sub>2</sub> enables radical addition of electron-deficient\nalkyl halides to acrylates, acrylamides, and vinyl sulfones in fair\nto excellent yields. The resultant ATRA products can be used in a\nvariety of telescoped reactions, including substitution with basic\namine nucleophiles to afford α-amino esters. The synthetic utility\nof the products is further demonstrated through derivatization to\ngive substituted cyclopropanes and a γ,δ-unsaturated ester.

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Genetic diversity and population structure
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A General Platform\nfor Copper-Catalyzed Atom Transfer\nRadical Addition with Electron-Deficient Olefins · Figshare (2024) | TGRS Research Map | TGRS