20469-72-1

Basic information

• Product Name: phenylboronic acid-d₂
• Synonyms: phenylboronic acid-d₂
• CAS NO: 20469-72-1
• Molecular Weight: 123.915
• Mol File: 20469-72-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: phenylboronic acid-d₂(CAS DataBase Reference)
• NIST Chemistry Reference: phenylboronic acid-d₂(20469-72-1)
• EPA Substance Registry System: phenylboronic acid-d₂(20469-72-1)

Safety Data

• Hazardous Substances Data: 20469-72-1(Hazardous Substances Data)

Upstream product

• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 7789-20-0 water-d2 
• 28249-75-4 2-phenyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 
• 109674-45-5 4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide 
• 1160553-64-9 5-phenyl-5,6-dihydrobenzo[e]pyrazolo[1,5-c][1,3,2]diazaborinine 
• 3559-74-8 trimethylsilylcyclopentadiene 
• 873-51-8 phenylborondichloride 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Downstream Products

• 1040880-60-1 ethyl (E)-3-phenyl-2-deuterobut-2-enoate 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 42858-44-6 ethyl (Z)-2-phenylbut-2-enoate 
• 1033424-99-5 C₁₅H₁₉⁽²⁾HO₂ 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 1821-12-1 4-Phenylbutyric acid 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 4119-41-9 1-iodo-3-phenylpropan 
• 127322-95-6 1-nitro-5-phenylpentan-2-one 
• 1449300-08-6 4-phenyl-N-(quinolin-8-yl)butanamide 
• 4789-06-4 (1-oxido-2-pyridinyl)phenylmethanone 
• 19125-73-6 4-deuterated-N,N-dimethylaniline 
• 78462-92-7 diisopropyl (2,2-diphenylvinyl)phosphonate 

Relevant articles and documents

Rhodium-Catalyzed Pyridine N-Oxide Assisted Suzuki-Miyaura Coupling Reaction via C(O)-C Bond Activation

A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp2) and C(O)-C(sp3) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones.

Synthesis of β,β-disubstituted indanones via the Pd-catalyzed tandem conjugate addition/cyclization reaction of arylboronic acids with α,β-unsaturated esters

Under Pd catalysis with a newly synthesized electron-deficient heterocycle, 2-(4,5-dihydroimidazol-2-yl)- pyrimidine (as the ligand), the reaction of α,β-unsaturated esters with arylboronic acids afforded a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. Mechanistic studies revealed that the reaction involves a tandem conjugate addition/1,4-Pd shift followed by a cyclization.

Single-isomer trisubstituted olefins from a novel reaction of (E)-βchloro-α-iodo-α,β-unsaturated esters and amides

(Chemical Equation Presented) (E)-β-Chloro-α-iodo-α, β-unsaturated esters are converted to single isomer trisubstituted olefins bearing three different carbon substituents by cross-coupling under reflux. Mechanistic investigations suggest that this process transfers a hydrogen from the boronic acid to the α-position of the substrate and then introduces an aryl group to the β-position of the intermediate template while replacing chloride. The reaction is highly stereoselective, showing preference for the E-isomer. The process proceeds through (E)-β-chloro-α-aryl-α, β-unsaturated esters that are transformed efficiently into the corresponding E-products through stereoselective Suzuki-type reactions giving single isomers. The observed stereo-chemistry is apparently enabled by the intermediacy of a palladium allenoate. The reaction involves a catalytic cycle in which PdII is reduced to Pd0 through the formation of biaryl-coupled products.