Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols

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,...

Descripción completa

Detalles Bibliográficos
Autores principales: Amos, Stephanie G. E., Nicolai, Stefano, Waser, Jerome
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162387/
https://www.ncbi.nlm.nih.gov/pubmed/34094368
http://dx.doi.org/10.1039/d0sc03655b
_version_ 1783700701617061888
author Amos, Stephanie G. E.
Nicolai, Stefano
Waser, Jerome
author_facet Amos, Stephanie G. E.
Nicolai, Stefano
Waser, Jerome
author_sort Amos, Stephanie G. E.
collection PubMed
description 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.
format Online
Article
Text
id pubmed-8162387
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-81623872021-06-04 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 Chem Sci Chemistry 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. The Royal Society of Chemistry 2020-09-22 /pmc/articles/PMC8162387/ /pubmed/34094368 http://dx.doi.org/10.1039/d0sc03655b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Amos, Stephanie G. E.
Nicolai, Stefano
Waser, Jerome
Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
title Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
title_full Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
title_fullStr Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
title_full_unstemmed Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
title_short Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
title_sort photocatalytic umpolung of n- and o-substituted alkenes for the synthesis of 1,2-amino alcohols and diols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162387/
https://www.ncbi.nlm.nih.gov/pubmed/34094368
http://dx.doi.org/10.1039/d0sc03655b
work_keys_str_mv AT amosstephaniege photocatalyticumpolungofnandosubstitutedalkenesforthesynthesisof12aminoalcoholsanddiols
AT nicolaistefano photocatalyticumpolungofnandosubstitutedalkenesforthesynthesisof12aminoalcoholsanddiols
AT waserjerome photocatalyticumpolungofnandosubstitutedalkenesforthesynthesisof12aminoalcoholsanddiols

Ejemplares similares