35369-98-3

Upstream product

• 617-86-7 triethylsilane 
• 1109-15-5 tris(pentafluorophenyl)borate 
• 363-72-4 Pentafluorobenzene 
• 10467-10-4 ethylmagnesium iodide 
• 27490-05-7 (pentafluoro phenyl) tribromo silane 
• 925-90-6 ethylmagnesium bromide 

Relevant academic research and scientific papers

Kinetic and mechanistic studies of the transformation of the catalyst, tris(pentafluorophenyl)borane, in the presence of silyl and germyl hydrides

Tris(pentafluorophenyl)borane catalyzed Si-H bond activation opens the door to numerous transition-metal-free reduction processes and is widely used in organic and polymer chemistry. However, chemical stability of B(C6F5)3 in the presence of silyl hydrides is limited, which can strongly affect its catalytic activity. Transformations of B(C6F5)3 in the presence of phenyldimethylsilane, triethylsilane and triethylgermane were studied by 19F NMR and UV spectroscopy, GC/MS and quantum-mechanical calculations. The observed exchange of pentafluorophenyl group attached to boron to hydrogen results in the formation of bis(pentafluorophenyl)borane, which has a strongly reduced ability to activate the Si-H bond. The substitution kinetics were studied by following the disappearance of absorption of the B(C6F5)3 charge transfer peak in the UV spectrum. Complementary quantum mechanical calculations allowed us to propose a mechanism of the ligand exchange reaction, which involves electrophilic substitution of the pentafluorophenyl group through a four-center transition state.

Palladium/Copper Dual Catalysis for the Cross-Coupling of Aryl(trialkyl)silanes with Aryl Bromides

Whereas aryl(trialkyl)silanes are considered to be ideal organometallic reagents for cross-coupling reactions owing to their stability, low toxicity, solubility, and easy accessibility, they are generally inert under typical cross-coupling conditions. Disclosed herein is a palladium/copper catalytic system that enables the cross-coupling of trimethyl, triethyl, tert-butyldimethyl, and triisopropyl aryl silanes with aryl bromides. This process is applicable to the sequential C?H and C?Si bond arylation of thiophenes and the synthesis of poly(thiophene–fluorene)s.