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

09 June 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


Photoredox Catalysis
Alkene Functionalization
Hypervalent Iodine
Amino alcohols


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