Uses
Catalyst for:
- Preparation of dicyano(aryl)cyclohexenecarboxylic acid esters via regioselective annulation
- Diastereoselective cycloaddition of styrenyl allenoates
- Interfacial carbonylation of methylbenzyl bromide
- Hydroformylation of octene
Reducing agent for selectivity of disulfide-internally linked peptide-nucleic acid cleavage
reaction suitability
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
Synthesis
Grignard reagent was prepared by adding 50 g of 4-bromo-N,N-dimethylaniline, 7 g of magnesium shavings, and 400 mL of anhydrous tetrahydrofuran (THF) to a 1 L three-necked flask under nitrogen protection, and the reaction was carried out at reflux for 10 hours. After the reaction was completed, it was cooled to room temperature, 2.9 g of tetrakis(triphenylphosphine)palladium was added and stirred for 3 hours. Subsequently, 61 g of diphenylphosphonium chloride was slowly added dropwise at room temperature, and after completion of the dropwise addition, the reaction mixture was refluxed for 8 hours. At the end of the reaction, the mixture was slowly added dropwise to 200 mL of reaction solution under cooling in an ice water bath. The reaction was quenched with saturated aqueous ammonium chloride solution and the organic phase was separated. The organic phase was crystallized by addition of methanol and filtered to give 74 g of white solid 4-(N,N-dimethylamino)triphenylphosphine in 96% yield.
References
[1] Patent: CN105859774, 2016, A. Location in patent: Paragraph 0090; 0091; 0092; 0093
[2] Journal of Organometallic Chemistry, 1999, vol. 575, # 1, p. 63 - 66
[3] Russian Journal of General Chemistry, 2000, vol. 70, # 4, p. 524 - 528
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 37 - 41
[5] Chemische Berichte, 1984, vol. 117, # 9, p. 2791 - 2802
