88208-13-3

Upstream product

• 766-90-5 cis-1-phenyl-1-propylene 
• 873-66-5 1-propenylbenzene 
• 64578-01-4 C₁₁H₁₀F₄O₂ 
• 21120-36-5 1-fluoroethyl phenyl ketone 

Downstream Products

• 698-87-3 3-phenyl-2-propanol 
• 93-54-9 1-Phenyl-1-propanol 
• 1123-85-9 (RS)-2-phenyl-1-propanol 
• 21120-36-5 1-fluoroethyl phenyl ketone 

Relevant academic research and scientific papers

Palladium-catalyzed intermolecular fluoroesterification of styrenes: Exploration and mechanistic insight

A novel palladium-catalyzed intermolecular oxidative fluoroesterification of vinylarenes has been developed using NFSI, one of the mildest electrophilic fluorinating reagents. The reaction presents an efficient synthetic pathway to afford a series of α-monofluoromethylbenzyl carboxylates in good to excellent yields. Rather than following an electrophilic fluorination pathway, the reaction is initiated through oxidation of Pd(0) to a Pd(ii) fluoride complex by NFSI, followed by fluoropalladation of a styrene to generate an α-monofluoromethylbenzyl-Pd intermediate. Generally, reductive elimination of benzyl-PdII complexes is favored with relatively strong oxy-nucleophiles to afford C-O bonds. This reaction, however, exhibited the opposite reactivity: strong acids with weak nucleophilicity, such as CF 3CO2H and CCl3CO2H, were prone to afford the fluoroesterification product, while weak acids with strong nucleophilicity, such as HOAc and BzOH, did not deliver the C-O bond product. Further mechanistic studies determined that Csp3-Pd(O2CR), a key intermediate, was generated through ionic ligand exchange between benzyl-Pd(NZ2) and CF3CO2H, and the final C-O bond was possibly formed through reductive elimination of a high-valent Csp 3-Pd(O2CR) complex via an SN2-type nucleophilic attack pathway.

Reduction of Organofluorine Compounds with Lithium Triethylborohydride

The reductive cleavage of the C-F bond with lithium triethylborohydride is strongly retarded by steric hindrance but is accelerated by adjacent hydroxyl groups in the organofluorine compound (Table 1).The effect of the hydroxyl group is stongest when it is tertiary, and compounds having such hydroxyl groups are evidently reduced exclusively via epoxides.