Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols |
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| Authors: | Stephanie G E Amos Stefano Nicolai Jerome Waser |
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| Institution: | Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, Ch-1015 Lausanne Switzerland, |
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| Abstract: | We report an organophotocatalytic 1,2-oxyalkynylation of ene-carbamates and enol ethers using Ethynyl BenziodoXolones (EBXs). 1-Alkynyl-1,2-amino alcohols and diols were obtained in up to 89% yield. Photocatalytic formation of radical cations led to Umpolung of the innate reactivity of the alkenes, enabling addition of a nucleophilic benzoate followed by radical alkynylation.Photocatalytic Umpolung with organic dyes overcoming the innate nucleophilicity of enecarbamates and enol ethers for oxyalkynylation with EBX reagents to access 1-alkynyl-1,2-amino alcohols and diols. |
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