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

Xiang Liu,^a Cai-Yu He,^a Hao-Nan Yin,^a Chengping Miao,^b Xue-Qiang Chu,^a Weidong Rao,^c Hao Xu,*^a Xiaocong Zhou,*^b Zhi-Liang Shen*^a

^a Technical 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.

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

^c Jiangsu 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 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.

Chinese Journal of Chemistry 2023, 41, 3539-3546. (Impact factor: 5.4)

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