Recent Strategies for Carbon−Halogen Bond Formation Using Nickel

• Published in: Angewandte Chemie International Edition 2021-07, Vol.60 (31), p.16750-16762
• Main Authors: Marchese, Austin D., Adrianov, Timur, Lautens, Mark
• Format: Article
• Language: English
• Subjects: Aromatic compounds; carboiodination; Carbonyl compounds; Carbonyls; Catalysis; Chemical reactions; C−H functionalization; Enantiomers; Fluorination; Halogenation; halogens; Nickel
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202101324

Nickel catalysis has demonstrated the capability of performing a broad range of synthetically challenging transformations over the last decade. Though recent literature has focused on the formation of C−C and C−N bonds, a variety of breakthroughs in the field of C−X bond generation have also been reported. A diverse range of strategies using nickel have been developed, in an effort to expand the scope and synthetic utility of these halogenation methods. This Minireview will cover six emerging strategies in this field including: oxidatively induced C−X reductive elimination, triflate‐to‐halogen exchange reactions, directed C−H halogenation, non‐directed electrophilic C−H halogenation of arenes, enantioselective α‐fluorination of carbonyl containing compounds, and 1,2‐difunctionalization‐halogenation reactions. The final section has been split into two parts: nickel‐catalyzed hydrohalogenation and nickel‐catalyzed carbohalogenation reactions. A diverse range of halogenation strategies using nickel have been developed over the past decade. This Minireview will cover six emerging strategies in this field including: oxidatively induced C−X reductive elimination, triflate‐to‐halogen exchange, directed C−H halogenation, non‐directed electrophilic C−H halogenation, enantioselective α‐fluorination, and 1,2‐difunctionalization–halogenation reactions including hydrohalogenation and carbohalogenation reactions.