Cargando…
Base Metal-Catalyzed Direct Olefinations of Alcohols with Sulfones
[Image: see text] Herein, a base-metal nickel-catalyzed direct olefination of alcohols with sulfones is reported. The reaction operates under low catalyst loading and does not require an external redox reagent. A wide range of trans-stilbenes and styrenes were synthesized in good yields and selectiv...
Autores principales: | , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648817/ https://www.ncbi.nlm.nih.gov/pubmed/31459819 http://dx.doi.org/10.1021/acsomega.9b00567 |
_version_ | 1783437949888626688 |
---|---|
author | Waiba, Satyadeep Das, Animesh Barman, Milan K. Maji, Biplab |
author_facet | Waiba, Satyadeep Das, Animesh Barman, Milan K. Maji, Biplab |
author_sort | Waiba, Satyadeep |
collection | PubMed |
description | [Image: see text] Herein, a base-metal nickel-catalyzed direct olefination of alcohols with sulfones is reported. The reaction operates under low catalyst loading and does not require an external redox reagent. A wide range of trans-stilbenes and styrenes were synthesized in good yields and selectivities. Biologically active stilbene DMU-212 could also be synthesized in a single step under these conditions. Mechanistic studies involving kinetic isotope effect, deuterium labeling experiments, and catalytic and stoichiometric reactions with possible catalytic intermediates were performed to elucidate a plausible mechanism. |
format | Online Article Text |
id | pubmed-6648817 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66488172019-08-27 Base Metal-Catalyzed Direct Olefinations of Alcohols with Sulfones Waiba, Satyadeep Das, Animesh Barman, Milan K. Maji, Biplab ACS Omega [Image: see text] Herein, a base-metal nickel-catalyzed direct olefination of alcohols with sulfones is reported. The reaction operates under low catalyst loading and does not require an external redox reagent. A wide range of trans-stilbenes and styrenes were synthesized in good yields and selectivities. Biologically active stilbene DMU-212 could also be synthesized in a single step under these conditions. Mechanistic studies involving kinetic isotope effect, deuterium labeling experiments, and catalytic and stoichiometric reactions with possible catalytic intermediates were performed to elucidate a plausible mechanism. American Chemical Society 2019-04-18 /pmc/articles/PMC6648817/ /pubmed/31459819 http://dx.doi.org/10.1021/acsomega.9b00567 Text en Copyright © 2019 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 | Waiba, Satyadeep Das, Animesh Barman, Milan K. Maji, Biplab Base Metal-Catalyzed Direct Olefinations of Alcohols with Sulfones |
title | Base Metal-Catalyzed Direct Olefinations of Alcohols
with Sulfones |
title_full | Base Metal-Catalyzed Direct Olefinations of Alcohols
with Sulfones |
title_fullStr | Base Metal-Catalyzed Direct Olefinations of Alcohols
with Sulfones |
title_full_unstemmed | Base Metal-Catalyzed Direct Olefinations of Alcohols
with Sulfones |
title_short | Base Metal-Catalyzed Direct Olefinations of Alcohols
with Sulfones |
title_sort | base metal-catalyzed direct olefinations of alcohols
with sulfones |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648817/ https://www.ncbi.nlm.nih.gov/pubmed/31459819 http://dx.doi.org/10.1021/acsomega.9b00567 |
work_keys_str_mv | AT waibasatyadeep basemetalcatalyzeddirectolefinationsofalcoholswithsulfones AT dasanimesh basemetalcatalyzeddirectolefinationsofalcoholswithsulfones AT barmanmilank basemetalcatalyzeddirectolefinationsofalcoholswithsulfones AT majibiplab basemetalcatalyzeddirectolefinationsofalcoholswithsulfones |