Original Article:
Pd-Catalyzed Boroperfluoroalkylation of Alkynes Opens a Route to One-Pot Reductive Carboperfluoroalkylation of Alkynes with Perfluoroalkyl and Aryl Iodides
Sylwester Domański et al.
Org. Lett. 2019, 21(13), 5021–5025.
10.1021/acs.orglett.9b01618
This study examines XPhos Pd G3-catalyzed three-component reaction enabling perfluoroalkylative borylation of terminal and internal alkynes with perfluoroalkyl iodide and (Bpin)2. Mechanistic studies have shown that the three-component reactions that make up this sequential transformation (i.e., iodine perfluoroformylation, boronation, and coupling) differ significantly in rate. Both electron rich and electron deficient iodenes are compatible with the reaction conditions with good yields (42-74%), and spatial steric hindrance is also well tolerated. Substrates containing various functional groups, including halogen, cyano, nitro, ester and unprotected formyl or hydroxyl functional groups, have been proved to be suitable for the reaction. This scheme represents the first example of reductive di carbon functionalization of alkynes with two electrophilic reagents, perfluoroalkyl and aryl iodides. Thus, the disclosed method is easy to control and can be easily controlled by temperatur, providing access to fluoroalkyl-substituted vinyl iodide, vinyl borate or alkene from the same complex reaction mixture.
Chemicals Related in the Paper:
| Catalog Number | Product Name | Structure | CAS Number | Price |
|---|---|---|---|---|
| ACM1445085551-1 | XPhos Pd G3 |  |
1445085-55-1 | Price |
