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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...

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Autores principales: Waiba, Satyadeep, Das, Animesh, Barman, Milan K., Maji, Biplab
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
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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.
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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
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