Nickel-Catalyzed Cross-ElectrophileCoupling of Triazine Esterswith Aryl Bromides

Xiang Liu,^aCai-Yu He,^aHao-Nan Yin,^aChengping Miao,^bXue-Qiang Chu,^aWeidong Rao,^cHao Xu,*^aXiaocong Zhou,*^bZhi-Liang Shen*^a

^aTechnical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China. E-mail: xuhao@njtech.edu.cn;ias_zlshen@njtech.edu.cn.

^bCollege of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, China.E-mail:xczhou@zjxu.edu.cn.

^cJiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

Abstract:Cross-electrophile coupling of triazine esters with aryl bromidescouldbe 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.

Chinese Journal of Chemistry2023,41, 3539-3546. (Impact factor: 5.4)

论文链接：https://doi.org/10.1002/cjoc.202300399