Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
Amos, Stephanie G. E.; Nicolai, Stefano; Waser, Jerome
2020

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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.

Details

Title Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
Author(s) Amos, Stephanie G. E. ; Nicolai, Stefano ; Waser, Jerome
Published in Chemical Science
Volume 11
Issue 41
Pages 11274-11279
Date 2020-11-07
ISSN 2041-6520
2041-6539
Keywords
DOI https://doi.org/10.1039/d0sc03655b
Other identifier(s) View record in Web of Science
Dataset(s) URL: https://doi.org/10.5281/zenodo.4043189
Laboratories LCSO
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LCSO - Laboratory of Catalysis and Organic Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2020-11-24

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