Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones

[Image: see text] A protocol for silver-catalyzed controlled intermolecular cross-coupling of silyl enolates is disclosed. The protocol displays good functional group tolerance and allows efficient preparation of a series of synthetically useful 1,4-diketones. Preliminary mechanistic investigations...

Descripción completa

Detalles Bibliográficos
Autores principales: Xu, Li, Liu, Xiaoyi, Alvey, Gregory R., Shatskiy, Andrey, Liu, Jian-Quan, Kärkäs, Markus D., Wang, Xiang-Shan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9536665/
https://www.ncbi.nlm.nih.gov/pubmed/35713416
http://dx.doi.org/10.1021/acs.orglett.2c01477
_version_ 1784803031000285184
author Xu, Li
Liu, Xiaoyi
Alvey, Gregory R.
Shatskiy, Andrey
Liu, Jian-Quan
Kärkäs, Markus D.
Wang, Xiang-Shan
author_facet Xu, Li
Liu, Xiaoyi
Alvey, Gregory R.
Shatskiy, Andrey
Liu, Jian-Quan
Kärkäs, Markus D.
Wang, Xiang-Shan
author_sort Xu, Li
collection PubMed
description [Image: see text] A protocol for silver-catalyzed controlled intermolecular cross-coupling of silyl enolates is disclosed. The protocol displays good functional group tolerance and allows efficient preparation of a series of synthetically useful 1,4-diketones. Preliminary mechanistic investigations suggest that the reaction proceeds through a one-electron process involving free radical species in which PhBr acts as the oxidant.
format Online
Article
Text
id pubmed-9536665
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-95366652022-10-07 Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones Xu, Li Liu, Xiaoyi Alvey, Gregory R. Shatskiy, Andrey Liu, Jian-Quan Kärkäs, Markus D. Wang, Xiang-Shan Org Lett [Image: see text] A protocol for silver-catalyzed controlled intermolecular cross-coupling of silyl enolates is disclosed. The protocol displays good functional group tolerance and allows efficient preparation of a series of synthetically useful 1,4-diketones. Preliminary mechanistic investigations suggest that the reaction proceeds through a one-electron process involving free radical species in which PhBr acts as the oxidant. American Chemical Society 2022-06-17 2022-07-01 /pmc/articles/PMC9536665/ /pubmed/35713416 http://dx.doi.org/10.1021/acs.orglett.2c01477 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Xu, Li
Liu, Xiaoyi
Alvey, Gregory R.
Shatskiy, Andrey
Liu, Jian-Quan
Kärkäs, Markus D.
Wang, Xiang-Shan
Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones
title Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones
title_full Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones
title_fullStr Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones
title_full_unstemmed Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones
title_short Silver-Catalyzed Controlled Intermolecular Cross-Coupling of Silyl Enol Ethers: Scalable Access to 1,4-Diketones
title_sort silver-catalyzed controlled intermolecular cross-coupling of silyl enol ethers: scalable access to 1,4-diketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9536665/
https://www.ncbi.nlm.nih.gov/pubmed/35713416
http://dx.doi.org/10.1021/acs.orglett.2c01477
work_keys_str_mv AT xuli silvercatalyzedcontrolledintermolecularcrosscouplingofsilylenolethersscalableaccessto14diketones
AT liuxiaoyi silvercatalyzedcontrolledintermolecularcrosscouplingofsilylenolethersscalableaccessto14diketones
AT alveygregoryr silvercatalyzedcontrolledintermolecularcrosscouplingofsilylenolethersscalableaccessto14diketones
AT shatskiyandrey silvercatalyzedcontrolledintermolecularcrosscouplingofsilylenolethersscalableaccessto14diketones
AT liujianquan silvercatalyzedcontrolledintermolecularcrosscouplingofsilylenolethersscalableaccessto14diketones
AT karkasmarkusd silvercatalyzedcontrolledintermolecularcrosscouplingofsilylenolethersscalableaccessto14diketones
AT wangxiangshan silvercatalyzedcontrolledintermolecularcrosscouplingofsilylenolethersscalableaccessto14diketones

Ejemplares similares