Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst

[Image: see text] An operationally simple, mild, redox-neutral method for the photoredox alkylation of imines is reported. Utilizing an inexpensive organic photoredox catalyst, alkyl radicals are readily generated from the single-electron oxidation of ammonium alkyl bis(catecholato)silicates and are...

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Autores principales: Patel, Niki R., Kelly, Christopher B., Siegenfeld, Allison P., Molander, Gary A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369175/
https://www.ncbi.nlm.nih.gov/pubmed/28367354
http://dx.doi.org/10.1021/acscatal.6b03665
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author Patel, Niki R.
Kelly, Christopher B.
Siegenfeld, Allison P.
Molander, Gary A.
author_facet Patel, Niki R.
Kelly, Christopher B.
Siegenfeld, Allison P.
Molander, Gary A.
author_sort Patel, Niki R.
collection PubMed
description [Image: see text] An operationally simple, mild, redox-neutral method for the photoredox alkylation of imines is reported. Utilizing an inexpensive organic photoredox catalyst, alkyl radicals are readily generated from the single-electron oxidation of ammonium alkyl bis(catecholato)silicates and are subsequently engaged in a C–C bond-forming reaction with imines. The process is highly selective, metal-free, and does not require a large excess of the alkylating reagent or the use of acidic additives.
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spelling pubmed-53691752018-02-06 Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst Patel, Niki R. Kelly, Christopher B. Siegenfeld, Allison P. Molander, Gary A. ACS Catal [Image: see text] An operationally simple, mild, redox-neutral method for the photoredox alkylation of imines is reported. Utilizing an inexpensive organic photoredox catalyst, alkyl radicals are readily generated from the single-electron oxidation of ammonium alkyl bis(catecholato)silicates and are subsequently engaged in a C–C bond-forming reaction with imines. The process is highly selective, metal-free, and does not require a large excess of the alkylating reagent or the use of acidic additives. American Chemical Society 2017-02-06 2017-03-03 /pmc/articles/PMC5369175/ /pubmed/28367354 http://dx.doi.org/10.1021/acscatal.6b03665 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Patel, Niki R.
Kelly, Christopher B.
Siegenfeld, Allison P.
Molander, Gary A.
Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst
title Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst
title_full Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst
title_fullStr Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst
title_full_unstemmed Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst
title_short Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst
title_sort mild, redox-neutral alkylation of imines enabled by an organic photocatalyst
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5369175/
https://www.ncbi.nlm.nih.gov/pubmed/28367354
http://dx.doi.org/10.1021/acscatal.6b03665
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AT molandergarya mildredoxneutralalkylationofiminesenabledbyanorganicphotocatalyst

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