41920-24-5

Upstream product

• 589-87-7 1,4-bromoiodobenzene 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 41920-29-0 C₁₆H₁₈BrN₂O₅PS 
• 33493-31-1 p-Brombenzoyl-dimethyl-phosphonat 

Relevant academic research and scientific papers

Rh(I)-Catalyzed Arylation of α-Diazo Phosphonates with Aryl Boronic Acids: Synthesis of Diarylmethylphosphonates

An efficient synthetic method for diarylmethylphosphonates is presented. A series of phosphonate derivatives with diverse functional groups can be accessed via a rhodium catalyzed cross-coupling reaction between α-diazo phosphonates and aryl boronic acids. Migratory insertion of rhodium carbene intermediates is postulated to be the critical step in this transformation.

Geminal difunctionalization of α-diazo arylmethylphosphonates: Synthesis of fluorinated phosphonates

A general approach towards diverse fluorinated phosphonates via geminal difunctionalization reactions of α-diazo arylmethylphosphonates is described. The diazo functionality (RR′CN2) is successfully converted to RR′CF2, RR′CHF, RR′CFBr or RR′CFNR′′2 groups by employing different fluorination reagents. A variety of fluorinated organophosphorus compounds were readily accessed in good to excellent yields from a common type of precursor.

Cu(I)-Catalyzed Tandem Reaction of Carbene Coupling and Horner-Wadsworth-Emmons Type Olefination: Access toward Enynes

A novel strategy to synthesize 1,3-enynes has been successfully developed based on Cu(I)-catalyzed cross-coupling of α-diazo phosphonates and alkynes with a subsequent Horner-Wadsworth-Emmons (HWE) type reaction. This method provides straightforward access to conjugated enynes with high efficiency, good stereoselectivity and excellent functional group compatibility. Copper(I) carbene migratory insertion plays a crucial role in this transformation.

Synthesis of Alkenylphosphonates through Palladium-Catalyzed Coupling of α-Diazo Phosphonates with Benzyl or Allyl Halides

An efficient method for the synthesis of organophosphonates through palladium-catalyzed coupling of α-diazo phosphonates with benzyl or allyl halides has been developed. Trisubstituted alkenylphosphonates bearing versatile functional groups can be easily accessed in good yields and with excellent stereoselectivity through this method. Moreover, with similar strategy α-substituted vinylphosphonates can also be attained by the palladium-catalyzed coupling reaction of N-tosylhydrazones and aryl bromides. Migratory insertion of palladium carbene is proposed as the key step in this reaction.

Synthesis of Aryldiazoacetates through Palladium(0)-Catalyzed Deacylative Cross-Coupling of Aryl Iodides with Acyldiazoacetates

Palladium(0)-catalyzed deacylative cross-coupling of aryl iodides and acyldiazocarbonyl compounds can be achieved at room temperature under mild reaction conditions. The coupling reaction represents a highly efficient and general method for the synthesis of aryldiazocarbonyl compounds, which have found wide and increasing applications as precursors for generating donor/acceptor-substituted metallocarbenes.