Organic Letters
Organic Letters
5 years ago

Nickel(II)-Catalyzed Site-Selective C–H Bond Trifluoromethylation of Arylamine in Water through a Coordinating Activation Strategy

Nickel(II)-Catalyzed Site-Selective C–H Bond Trifluoromethylation of Arylamine in Water through a Coordinating Activation Strategy
Chao Shen, Pengfei Zhang, Jiabin Shen, Kejie Chai, Jun Xu, Li Qiao
The first example of nickel(II)-catalyzed site-selective C–H bond trifluoromethylation of arylamine in water is established. In this transformation, a coordinating activation strategy is performed by the utilization of picolinamide as a directing group, and target products are obtained in moderate to good yields. In addition, the catalyst-in-water system can be reutilized eight times with a slight loss of catalytic activity and applied in the green, concise synthesis of acid red 266. Furthermore, a series of control experiments verify that a single-electron transfer mechanism is responsible for this reaction.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02823

DOI: 10.1021/acs.orglett.7b02823

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