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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
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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 |
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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 |