Coordinating Activation Strategy‐Induced Selective C−H Trifluoromethylation of Anilines. Issue 5 (6th February 2018)

• Record Type: Journal Article
• Authors: Xu, Jun; Cheng, Ke; Shen, Chao; Bai, Renren; Xie, Yuanyuan; Zhang, Pengfei
• Is Part Of: ChemCatChem. Volume 10:Issue 5(2018)
• Page Start: 965
• Page End: 970
• Publication Date: 2018-02-06
• Subjects: anilines -- coordinating activation -- electron transfer -- fluorine -- trifluoromethylation; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201701596
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: A simple protocol for the synthesis of 2‐(trifluoromethyl)aniline derivatives through a coordinating activation strategy was developed. The reaction showed good reactivity and gave the target products in moderate to good yields. Pleasingly, the directing group could be recovered in excellent yield. Furthermore, this strategy allowed efficient access to the synthesis of floctafenine. A single‐electron‐transfer mechanism was proposed to be responsible for this trifluoromethylation reaction. Abstract : Pic'd curiosity : A simple protocol for the synthesis of 2‐(trifluoromethyl)aniline derivatives through Cu‐catalyzed picolinamide‐directed C−H trifluoromethylation is developed. The reaction shows good reactivity and gives the target products in moderate to good yields. Furthermore, the directing group can be recovered in excellent yield. Application of this strategy to the synthesis of floctafenine is demonstrated, and a plausible mechanism is proposed.