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Three-Component Aminoarylation of Electron-Rich Alkenes by Merging Photoredox with Nickel Catalysis.

ABSTRACT: A three-component 1,2-aminoarylation of vinyl ethers, enamides, ene-carbamates and vinyl thioethers by synergistic photoredox and nickel catalysis is reported. 2,2,2-Trifluoroethoxy carbonyl protected α-amino-oxy acids are used as amidyl radical precursors. anti-Markovnikov addition of the amidyl radical to the alkene and Ni-mediated radical/transition metal cross over lead to the corresponding 1,2-aminoarylation product. The radical cascade, which can be conducted under practical and mild conditions, features high functional group tolerance and broad substrate scope. Stereoselective 1,2-aminoarylation is achieved using a L-(+)-lactic acid derived vinyl ether as the substrate, offering a novel route for the preparation of protected enantiopure α-arylated β-amino alcohols. In addition, 1,2-aminoacylation of vinyl ethers is achieved by using an acyl succinimide as the electrophile for the Ni-mediated radical coupling.

SUBMITTER: Jiang H

PROVIDER: S-EPMC8252614 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Three-Component Aminoarylation of Electron-Rich Alkenes by Merging Photoredox with Nickel Catalysis.

Jiang Heng H Yu Xiaoye X Daniliuc Constantin G CG Studer Armido A

Angewandte Chemie (International ed. in English) 20210519 26

A three-component 1,2-aminoarylation of vinyl ethers, enamides, ene-carbamates and vinyl thioethers by synergistic photoredox and nickel catalysis is reported. 2,2,2-Trifluoroethoxy carbonyl protected α-amino-oxy acids are used as amidyl radical precursors. anti-Markovnikov addition of the amidyl radical to the alkene and Ni-mediated radical/transition metal cross over lead to the corresponding 1,2-aminoarylation product. The radical cascade, which can be conducted under practical and mild condi ...[more]

PMID: 33871137

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