33715-53-6

Upstream product

• 78-10-4 tetraethoxy orthosilicate 
• 352-13-6 4-flourophenylmagnesium bromide 
• 460-00-4 1-Bromo-4-fluorobenzene 

Downstream Products

• 13272-84-9 (4-fluorophenyl)silane 
• 1186241-75-7 N-(3-(4-fluorophenyl)-2H-chromen-4-yl)acetamide 
• 397-54-6 2-(4-fluorophenyl)benzoxazole 
• 345-83-5 4-fluorobenzophenone 
• 310-40-7 diethyl (4-fluorophenyl)phosphonate 
• 324-74-3 4-fluoro-biphenyl 
• 4280-40-4 4-(4-fluorophenyl)morpholine 
• 88229-29-2 N,N-dibenzyl-4-fluorobenzamide 
• 1057224-07-3 3-(4-fluorophenyl)-1-methylquinoxalin-2(1H)-one 
• 1341224-06-3 dodecyl 4-fluorobenzenethioate 
• 130754-17-5 ethyl 2-fluoro-2-(4-fluorophenyl)acetate 
• 1582806-71-0 (S)-3-(4-fluorophenyl)-2-phthalimido-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide 
• 398-23-2 4,4'-difluorobiphenyl 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes

The stereoselective β-C(sp2)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.

The Hiyama Cross-Coupling Reaction at Parts Per Million Levels of Pd: In Situ Formation of Highly Active Spirosilicates in Glycol Solvents

A palladium NNC-pincer complex at a 5 mol ppm loading efficiently catalyzed the Hiyama coupling reaction of aryl bromides with aryl(trialkoxy)silanes in propylene glycol to give the corresponding biaryls in excellent yields. This method was applied to the syntheses of adapalene and a biaryl-type liquid-crystalline compound, as well as to the derivatization of dextromethorphan and norfloxacin. ESI-MS and NMR analyses of the reaction mixture suggested the formation of pentacoordinate spirosilicate intermediates in situ. Preliminary theoretical studies revealed that the glycol-derived silicate intermediates formed in situ are quite reactive silicon reagents in the transmetalation step.

Ligand-promoted oxidative cross-coupling of aryl boronic acids and aryl silanes by palladium catalysis

The first cross-coupling reaction between aryl silanes and aryl boronic acids is described. This transformation represents one of the very few examples of coupling reactions between two nucleophilic organometallic reagents and provides a new method for the formation of biaryl compounds. The successful development of this reaction was enabled by the use of commercially available 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP) as the ligand. A small amount of BINAP (3 mol %) was sufficient to suppress the formation of the homocoupling products, and the reaction yielded the cross-coupling products with high selectivity under mild conditions, even when the ratio of the two coupling partners was 1:1.

One-pot synthesis and structural characterization of poly(alkoxysilane)s catalyzed by silver-gold complexes

Combinative one-pot Si-Si/Si-O dehydrocoupling of hydrosilanes with alcohols (1:1.5 mole ratio), mediated by a mixture of AgNO3-AuCl 3 (100/1 mole ratio) rapidly produced poly(alkoxysilane)s in reasonably high yield. The addition of small amount of gold complex to the reaction mixture effectively accelerated the coupling reaction compared to the reaction rate with AgNO3 alone. The hydrosilanes include p-X-C 6H4SiH3 (X = H, CH3, OCH 3, F), PhCH2SiH3, and (PhSiH2) 2. The alcohols include MeOH, EtOH, iPrOH, PhOH, and CF 3(CF2)2CH2OH. The weight average molecular weight and polydispersity of the poly(alkoxysilane)s were in the range of 1,600～8,000 Dalton and 1.4～3.5, respectively. The dehydrocoupling reactions of phenylsilane with ethanol (1:3 mole ratio) in the presence of the Ag-Au complexes gave only triethoxyphenylsilane. Copyright

One-pot synthesis of poly(alkoxysilane)s by Si-Si/Si-O dehydrocoupling of silanes with alcohols using Group IV and VIII metallocene complexes

Si-Si/Si-O dehydrocoupling reactions of silanes with alcohols (1:1.5 mole ratio), catalyzed by Cp2MCl2/Red-Al (M=Ti, Zr) and Cp2M′ (M′=Co, Ni), produced poly(alkoxysilane)s in one-pot in high yield. The silanes included p-X-C6H4SiH3 (X=H, CH3, OCH3, F), PhCH2SiH3, and (PhSiH2)2. The alcohols were MeOH, EtOH, iPrOH, PhOH, and CF3(CF2) 2CH2OH. The weight average molecular weight of the poly(alkoxysilane)s ranged from 600 to 8000. The dehydrocoupling reactions of phenylsilane with ethanol (1:1.5 mole ratio) using Cp2HfCl2/Red-Al and phenylsilane with ethanol (1:3 mole ratio) using Cp2TiCl2/Red-Al gave only triethoxyphenylsilane as product.