RaabPhos, an Air-Stable, Highly Active Ferrocenyl Phosphasilinane Ligand, for Palladium-Catalyzed C-C and C-N
Michael G Raab1, Oliver Trapp1, Dino Berthold1
1Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, Haus F, 81377 München, Germany.
Abstract:
The air-stable, highly active ferrocenyl phosphasilinane ligand RaabPhos has been synthesized in four steps from readily available starting materials. Although the ligand is not sterically overloaded, it is highly electron-rich and therefore the corresponding Pd catalyst of high activity. Furthermore, RaabPhos is air-stable as a solid as well as in solution. With the application of this novel ligand in various Pd-catalyzed C-C and C-N bond-forming cross-coupling reactions, its reactivity toward unreactive (hetero)aryl chlorides has been explored. We observed, in general, high yields in these transformations under mild conditions.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
14:07Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Related Concept Videos
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Limitations of Friedel–Crafts Reactions
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)