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

Jun XuLi QiaoJiabin ShenKejie ChaiChao ShenPeng-Fei Zhang
Published in: Organic letters (2017)
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.
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