Nickel‐Catalyzed Reductive Coupling for Transforming Unactivated Aryl Electrophiles into β‐Fluoroethylarenes. Issue 1 (10th December 2019)

• Record Type: Journal Article
• Authors: Yang, Yi; Luo, Gen; Li, Youlin; Tong, Xia; He, Mengmeng; Zeng, Hongyao; Jiang, Yan; Liu, Yingle; Zheng, Yubin
• Is Part Of: Chemistry, an Asian journal. Volume 15:Issue 1(2020)
• Page Start: 156
• Page End: 162
• Publication Date: 2019-12-10
• Subjects: Homobenzylic Fluoride -- Methodology and Reactions -- Nickel -- Reductive Coupling -- Unactivated bond; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201901490
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: We report herein a facile synthetic method for converting unactivated (hetero)aryl electrophiles into β‐fluoroethylated (hetero)arenes via nickel‐catalyzed reductive cross‐couplings. This coupling reaction features the involvement of FCH2 CH2 radical intermediate rather than β‐fluoroethyl manganese species which provides effective solutions to the problematic β‐fluoride side eliminations. The practical value of this protocol is further demonstrated by the late‐stage modification of several complex ArCl or ArOH‐derived bioactive molecules. Abstract : Taking a Ni : We report herein a facile synthetic method for converting unactivated (hetero)aryl electrophiles into β‐fluoroethylated (hetero)arenes via nickel‐catalyzed reductive cross‐couplings. This method can be applied for the late‐stage modification of several complex ArCl or ArOH‐derived bioactive molecules with high efficiency.