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Accessing 1,2-Amino Alcohols and Diols through Photocatalytic Anti-Markovnikov Difunctionalisation of Ene-Carbamates and Enol Ethers

preprint
submitted on 08.06.2020 and posted on 09.06.2020 by Jerome Waser, Stefano Nicolai, Stephanie G. E. Amos
We report an atom-economical 1,2-oxyalkynylation of ene-carbamates and enol ethers based on the use of Ethynyl BenziodoXolone (EBX) as dual reagents for alkyne and oxygen transfer. The reaction occurs at room temperature under blue LED irradiation using an organic dye as a photocatalyst. A broad variety of 1-alkynyl-1,2-amino-alcohol and 1-alkynyl-1,2-diol scaffolds were obtained in up to 89% yield with anti-Markovnikov regioselectivity. The reaction is speculated to proceed via oxidation of the double bond to give a radical cation intermediate, enabling the selective difunctionalization of electron-rich alkenes.

History

Email Address of Submitting Author

jerome.waser@epfl.ch

Institution

EPFL Lausanne

Country

Switzerland

ORCID For Submitting Author

0000-0002-4570-914X

Declaration of Conflict of Interest

no conflict of interest

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