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ChemRXiv2020SGEA.pdf (12.04 MB)
Accessing 1,2-Amino Alcohols and Diols through Photocatalytic Anti-Markovnikov Difunctionalisation of Ene-Carbamates and Enol Ethers
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
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