![6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine structure](https://static.chemtradehub.com/structs/103/1033202-59-3-2a8f.webp "6-Bromo-3-ethyl-3H-imidazo[4,5-b]pyridine structure")
Palladium/norbornene/copper-catalysed intermolecular thio-esterification from ketones: modular access towards tetrasubstituted vinyl sulfides
Literature Information
Publication Date
2023-11-07
DOI
10.1039/D3QO01484C
Impact Factor
5.281
Authors
Guopeng Du, Yu Zhao, Pingliang Zhu, Shaowen Ling, Baolong Xu, Hui Liu, Xinjin Li, Feng-Gang Sun
View Original
Abstract
Herein, we disclosed a strategy to access diverse tetrasubstituted vinyl sulfides from cyclic ketones via palladium/norbornene/copper catalysed dual functionalization of the corresponding enol triflates, allowing simultaneous installation of thio and alkoxycarbonyl groups at vicinal positions of 1,2-disubstiuted alkene in a regioselective fashion. A copper salt was proven to enhance the reactivity of the electrophile to achieve the desired selectivity without using commonly used C2 amide-substituted norbornene. Readily available thiocarbonates are suitable bifunctional electrophiles; various functional groups could be tolerated. The protocol is scalable and permits orthogonal coupling in the presence of other functionalization handles.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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6,7-Dihydro-5H-pyrrolo[1,2-a]imidazole-6-carboxylic acid
CAS Number:
1369160-12-2
Molecular Formula:
C7H8N2O2
5,10,15,20-tetrakis(4-boronic acid pinacol ester phenyl) porphyrin
CAS Number:
1332748-00-1
Molecular Formula:
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Molecular Formula:
C23H20N4O4
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