Home Chemistry Organometallic Reagents Organoborons N,N-Diphenyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Aniline
Suzuki-Miyaura Cross-Coupling: This is one of the most common reactions involving boron-containing compounds like the one you mentioned. It involves the coupling of an aryl or vinyl boronate with an aryl or vinyl halide or triflate in the presence of a palladium catalyst. The result is the formation of a new carbon-carbon bond.
Grignard Reaction: N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline can react with a Grignard reagent (such as an alkyl or aryl magnesium halide) to form the corresponding boronic acid pinacol ester, which can then be further manipulated in various ways.
Buchwald-Hartwig Amination: This reaction allows for the introduction of nitrogen atoms into the molecule. By reacting the compound with an amine and a palladium catalyst, you can form an aryl-amine bond.
Hydrolysis: The boron-oxygen bond in the dioxaborolane ring can be hydrolyzed under acidic conditions to produce the corresponding boronic acid.
Substitution Reactions: The phenyl groups on the nitrogen atom are potential sites for substitution reactions with electrophiles.
Reduction Reactions: The nitro group can be reduced to an amine using reducing agents such as hydrogen gas or metal hydrides.
Oxidation Reactions: The boron atom can be oxidized to a boronic acid or other oxidation states using suitable reagents.
Protection and Deprotection: The dioxaborolane group can serve as a protecting group for alcohols, and it can be removed when needed using appropriate conditions.
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N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
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4-Methoxy-N-(4-methoxyphenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline
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4,4'-((4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azanediyl)dibenzaldehyde
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4-Methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-(p-tolyl)aniline
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4-Butyl-N-(4-butylphenyl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline
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