Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 1, Pages 135-143Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801824e
Keywords
-
Categories
Funding
- Danish National Research Foundation
- Danish Natural Science Research Council
- Carlsberg Foundation
- Lundbeck Foundation
Ask authors/readers for more resources
We report an initial investigation with the goal of determining the factors that control the 1,2-migration in the Negishi cross-coupling, which is promoted by palladium catalyst systems generated with JosiPhos ligands. Several of the factors that were demonstrated to be important for the 1,2-migration include (1) the nucleophilicity of the organometallic reagent, which possibly influences the transmetalation step in direct competition with the intermediate beta-hydride elimination of the alkenyl Pd(II) species; (2) the structural features of the vinyl tosylates and phosphates, in which substrates possessing a bulky Cl substituent displayed highest propensity for undergoing the 1,2-migration under the coupling reaction conditions: and (3) the structure of the JosiPhos ligand, where both the sterical bulk and choice of substituents on the ferrocenyl phosphino group greatly influence the catalytic activity of the palladium complex and its capacity to facilitate the 1,2-migration.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available