Nickel‐Catalyzed Cross‐Electrophile Coupling of Triazine Esters with Aryl Bromides

Comprehensive Summary Cross‐electrophile coupling of triazine esters with aryl bromides could be facilely accomplished by employing nickel as catalyst, magnesium as metal mediator, and lithium chloride as additive. The reactions proceeded efficiently in THF at room temperature through C—O bond activ...

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Bibliographic Details
Published in:Chinese journal of chemistry 2023-12, Vol.41 (24), p.3539-3546
Main Authors: Liu, Xiang, He, Cai‐Yu, Yin, Hao‐Nan, Miao, Chengping, Chu, Xue‐Qiang, Rao, Weidong, Xu, Hao, Zhou, Xiaocong, Shen, Zhi‐Liang
Format: Article
Language:English
Subjects:
Aromatic compounds
Bromides
Catalysts
Chemical reactions
Cross coupling
Esters
Functional groups
Ketones
Lithium
Lithium chloride
Magnesium
Nickel
Organometallic compounds
Reagents
Room temperature
Triazine
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Summary:Comprehensive Summary Cross‐electrophile coupling of triazine esters with aryl bromides could be facilely accomplished by employing nickel as catalyst, magnesium as metal mediator, and lithium chloride as additive. The reactions proceeded efficiently in THF at room temperature through C—O bond activation to afford an array of structurally different diaryl ketones in moderate to good yields with wide functional group tolerance. Control experiments showed that nickel, magnesium, lithium chloride, and THF are all indispensable for the good performance of the coupling reaction. Preliminary mechanistic exploration indicated that in situ formed arylmagnesium reagent by the insertion of magnesium into aryl bromide might serve as the key intermediate of the cross‐coupling. The method which avoids the utilization of moisture‐labile and relatively difficult‐to‐obtain organometallics is step‐economical, cost‐efficient, and operationally simple, potentially serving as an attractive alternative to documented methods.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202300399