13659-53-5

Upstream product

• 250212-41-0 2-fluoro-3-oxo-N-phenylbutanamide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 62-53-3 aniline 
• 103-80-0 phenylacetyl chloride 
• 22692-94-0 α-fluorophenylacetic acid chloride 
• 5110-77-0 N-phenyl-α-chlorophenylacetamide 
• 39982-78-0 α-bromophenylacetanilide 

Relevant academic research and scientific papers

Utilization of Unsymmetric Diaryliodonium Salts in α-Arylation of α-Fluoroacetoacetamides

The use of unsymmetric diaryliodonium salts as a versatile class of arylating agents has been demonstrated by developing a novel strategy to quickly access α-arylated α-fluoroacetoacetamides. The protocol provides a convenient metal-free method for the α-arylation of a diverse class of fluorinated acetoacetamides, and the products are obtained in good yields. The strategy, upon use of electron-deficient diaryliodonium salts as an arylating agent, provides α-fluoroacetamides through a spontaneous arylation/deacylation cascade.

Silver-Promoted Fluorination Reactions of α-Bromoamides

Silver-promoted C?F bond formation in α-bromoamides by using AgF under mild conditions is reported. This simple method enables access to tertiary, secondary, and primary alkyl fluorides involving biomolecular scaffolds. This transformation is applicable to primary and secondary amides and shows broad functional-group tolerance. Kinetics experiments revealed that the reaction rate increased in the order of 3°>2°>1° α-carbon atom. In addition, it was found that the acidic amide proton plays an important role in accelerating the reaction. Mechanistic studies suggested generation of an aziridinone intermediate that undergoes subsequent nucleophilic addition to form the C?F bond with stereospecificity (i.e., retention of configuration). The synthesis of sterically hindered alcohols and ethers by using AgI is also demonstrated. Examples of reactions of α-bromoamides with O nucleophiles are presented.

Decarbethoxylative Arylation Employing Arynes: A Metal-Free Pathway to Arylfluoroamides

An efficient, metal-free decarbethoxylative arylation protocol for the synthesis of α-aryl-α-fluoroamides from fluoromalonamates, under ambient reaction conditions using aryne as an electrophilic arylating agent, is reported. This decarbethoxylative arylation proceeds under mild conditions and provides a practical and effective entry to a wide range of α-aryl-α-fluoroacetamides. Interestingly, the use of the tert-butyl ester of fluoromalonamate prevented the otherwise rapid decarboxylation step, affording the arylated fluoromalonamate in moderate yield.

Tricomponent catalytic α,α-difluorination of acid chlorides

The selective α,α-difluorination of carbonyl compounds remains a challenge in modern organic synthesis; current methods often incorporate stepwise processes and/or harsh conditions, providing unsatisfactory mixtures of mono- and difluorinated products. In this communication, a practical, mild, and one-pot method for the selective α,α-difluorination of readily available acid chlorides is reported in which three separate catalysts act synergistically to form products in outstanding selectivity and fair to excellent yields.