1428-62-2

Usage

Appearance

Colorless liquid

Odor

Strong, sweet

Usage

Building block or intermediate in the synthesis of other compounds

Potential applications

Pharmaceuticals, agrochemicals, and materials science

Safety precautions

May be harmful if inhaled, ingested, or in contact with skin. Should be stored and disposed of following proper protocols to avoid environmental contamination or harm to human health.

Upstream product

• 201230-82-2 carbon monoxide 

Downstream Products

• 56530-31-5 1,3-diphenyl-4-phenylazopyrazole 
• 76073-56-8 1,1,2,2-tetrafluoropropiophenone phenylhydrazone 
• 76073-60-4 phenyldifluoromethylglyoxal bis-phenylhydrazone 
• 76073-63-7 1-phenyl-1-phenylazo-3-hydrotrifluoro-1-propene 

Relevant academic research and scientific papers

Controllable catalytic difluorocarbene transfer enables access to diversified fluoroalkylated arenes

Difluorocarbene has important applications in pharmaceuticals, agrochemicals and materials, but all these applications proceed using just a few types of reaction by taking advantage of its intrinsic electrophilicity. Here, we report a palladium-catalysed strategy that confers the formed palladium difluorocarbene (Pd=CF2) species with both nucleophilicity and electrophilicity by switching the valence state of the palladium centre (Pd(0) and Pd(ii), respectively). Controllable catalytic difluorocarbene transfer occurs between readily available arylboronic acids and the difluorocarbene precursor diethyl bromodifluoromethylphosphonate (BrCF2PO(OEt)2). From just this simple fluorine source, difluorocarbene transfer enables access to four types of product: difluoromethylated and tetrafluoroethylated arenes and their corresponding fluoroalkylated ketones. The transfer can also be applied to the modification of pharmaceuticals and agrochemicals as well as the one-pot diversified synthesis of fluorinated compounds. Mechanistic and computational studies consistently reveal that competition between nucleophilic and electrophilic palladium difluorocarbene ([Pd]=CF2) is the key factor controlling the catalytic difluorocarbene transfer.