Cargando…

Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds

[Image: see text] Generation of a ketyl radical from unactivated aliphatic carbonyl compounds is an important strategy in organic synthesis. Herein, catalytic generation and use of a ketyl radical for the reductive coupling of aliphatic carbonyl compounds and styrenes by organic photoredox catalysis...

Descripción completa

Detalles Bibliográficos
Autores principales: Seo, Hyowon, Jamison, Timothy F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6929042/
https://www.ncbi.nlm.nih.gov/pubmed/31820654
http://dx.doi.org/10.1021/acs.orglett.9b04235
_version_ 1783482612917993472
author Seo, Hyowon
Jamison, Timothy F.
author_facet Seo, Hyowon
Jamison, Timothy F.
author_sort Seo, Hyowon
collection PubMed
description [Image: see text] Generation of a ketyl radical from unactivated aliphatic carbonyl compounds is an important strategy in organic synthesis. Herein, catalytic generation and use of a ketyl radical for the reductive coupling of aliphatic carbonyl compounds and styrenes by organic photoredox catalysis is described. The method is applicable to both aliphatic ketones and aldehydes to afford the corresponding tertiary and secondary alcohols in continuous flow and batch. Preliminary mechanistic investigation suggests the catalytic formation of a ketyl radical intermediate.
format Online
Article
Text
id pubmed-6929042
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-69290422019-12-26 Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds Seo, Hyowon Jamison, Timothy F. Org Lett [Image: see text] Generation of a ketyl radical from unactivated aliphatic carbonyl compounds is an important strategy in organic synthesis. Herein, catalytic generation and use of a ketyl radical for the reductive coupling of aliphatic carbonyl compounds and styrenes by organic photoredox catalysis is described. The method is applicable to both aliphatic ketones and aldehydes to afford the corresponding tertiary and secondary alcohols in continuous flow and batch. Preliminary mechanistic investigation suggests the catalytic formation of a ketyl radical intermediate. American Chemical Society 2019-12-10 2019-12-20 /pmc/articles/PMC6929042/ /pubmed/31820654 http://dx.doi.org/10.1021/acs.orglett.9b04235 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Seo, Hyowon
Jamison, Timothy F.
Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
title Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
title_full Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
title_fullStr Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
title_full_unstemmed Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
title_short Catalytic Generation and Use of Ketyl Radical from Unactivated Aliphatic Carbonyl Compounds
title_sort catalytic generation and use of ketyl radical from unactivated aliphatic carbonyl compounds
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6929042/
https://www.ncbi.nlm.nih.gov/pubmed/31820654
http://dx.doi.org/10.1021/acs.orglett.9b04235
work_keys_str_mv AT seohyowon catalyticgenerationanduseofketylradicalfromunactivatedaliphaticcarbonylcompounds
AT jamisontimothyf catalyticgenerationanduseofketylradicalfromunactivatedaliphaticcarbonylcompounds