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

Xiang Liu, Cai Yu He, Hao Nan Yin, Chengping Miao, Xue Qiang Chu, Weidong Rao, Hao Xu, Xiaocong Zhou, Zhi Liang Shen

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)3539-3546
Number of pages8
JournalChinese Journal of Chemistry
Volume41
Issue number24
DOIs
StatePublished - 15 Dec 2023

Keywords

  • Cross-coupling
  • Cross-electrophile coupling
  • Diaryl ketones
  • Lithium chloride
  • Magnesium
  • Nickel
  • Triazine esters

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