Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO(2) extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophil...

Descripción completa

Detalles Bibliográficos
Autores principales: Donabauer, Karsten, Maity, Mitasree, Berger, Anna Lucia, Huff, Gregory S., Crespi, Stefano, König, Burkhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6524566/
https://www.ncbi.nlm.nih.gov/pubmed/31183069
http://dx.doi.org/10.1039/c9sc01356c
_version_ 1783419579313160192
author Donabauer, Karsten
Maity, Mitasree
Berger, Anna Lucia
Huff, Gregory S.
Crespi, Stefano
König, Burkhard
author_facet Donabauer, Karsten
Maity, Mitasree
Berger, Anna Lucia
Huff, Gregory S.
Crespi, Stefano
König, Burkhard
author_sort Donabauer, Karsten
collection PubMed
description We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO(2) extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.
format Online
Article
Text
id pubmed-6524566
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-65245662019-06-10 Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols Donabauer, Karsten Maity, Mitasree Berger, Anna Lucia Huff, Gregory S. Crespi, Stefano König, Burkhard Chem Sci Chemistry We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO(2) extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product. Royal Society of Chemistry 2019-04-16 /pmc/articles/PMC6524566/ /pubmed/31183069 http://dx.doi.org/10.1039/c9sc01356c Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by-nc/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Donabauer, Karsten
Maity, Mitasree
Berger, Anna Lucia
Huff, Gregory S.
Crespi, Stefano
König, Burkhard
Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
title Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
title_full Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
title_fullStr Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
title_full_unstemmed Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
title_short Photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
title_sort photocatalytic carbanion generation – benzylation of aliphatic aldehydes to secondary alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6524566/
https://www.ncbi.nlm.nih.gov/pubmed/31183069
http://dx.doi.org/10.1039/c9sc01356c
work_keys_str_mv AT donabauerkarsten photocatalyticcarbaniongenerationbenzylationofaliphaticaldehydestosecondaryalcohols
AT maitymitasree photocatalyticcarbaniongenerationbenzylationofaliphaticaldehydestosecondaryalcohols
AT bergerannalucia photocatalyticcarbaniongenerationbenzylationofaliphaticaldehydestosecondaryalcohols
AT huffgregorys photocatalyticcarbaniongenerationbenzylationofaliphaticaldehydestosecondaryalcohols
AT crespistefano photocatalyticcarbaniongenerationbenzylationofaliphaticaldehydestosecondaryalcohols
AT konigburkhard photocatalyticcarbaniongenerationbenzylationofaliphaticaldehydestosecondaryalcohols

Ejemplares similares