Difluorocarbene-based cyanodifluoromethylation of alkenes induced by a dual-functional Cu-catalyst
Min Zhang1, Jin-Hong Lin1, Chuan-Ming Jin2
1Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. jchxiao@sioc.ac.cn.
Abstract:
Although cyanofluoroalkylation has received increasing attention, a toxic cyanation reagent is usually required. Herein, a Cu-catalyzed difluorocarbene-based cyanodifluoromethylation of alkenes with BrCF2CO2Et/NH4HCO3 under photocatalytic conditions is described. BrCF2CO2Et and NH4HCO3 serve as a carbon source and a nitrogen source of the nitrile group, respectively, avoiding the use of a stoichiometric toxic cyanation reagent. The Cu-complex plays a dual role. It is not only a photocatalyst, but also a coupling catalyst for the formation of a C-CN bond.
Related Concept Videos
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Carboxylic Acids to Methylesters: Alkylation using Diazomethane
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Oxymercuration-Reduction of Alkenes
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction


![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)