Home Chemistry Organometallic Reagents Organoborons 2-Benzyl-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane
Suzuki-Miyaura Cross-Coupling: This is the most common reaction involving 2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. It is used to form carbon-carbon bonds by coupling the boron-containing compound with an organohalide (e.g., aryl bromide or chloride) in the presence of a palladium catalyst and a base. The result is the formation of a new carbon-carbon bond between the boron atom and the organic halide.
Hydroboration-Oxidation: 2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can undergo hydroboration reactions, where it reacts with an alkene or alkyne in the presence of boron reagents like borane or boron trifluoride, followed by oxidation with hydrogen peroxide or another oxidizing agent. This reaction can lead to the formation of organoboranes, which can be further functionalized.
Reduction: The compound can be reduced to its corresponding alcohol using reducing agents like sodium borohydride or lithium aluminum hydride. This reduction results in the replacement of the boron atom with a hydrogen atom.
Halogenation: 2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can undergo halogenation reactions, such as bromination or chlorination, when treated with halogenating agents in the presence of a Lewis acid catalyst. This reaction can introduce halogen substituents onto the benzyl group or boron atom.
Nucleophilic Substitution: The benzyl group in the compound can undergo nucleophilic substitution reactions when treated with appropriate nucleophiles under suitable conditions. This can lead to the formation of various derivatives of the compound.
Grignard Reaction: It can react with Grignard reagents to form new carbon-carbon bonds. This reaction is useful for the synthesis of complex organic molecules.
Boronic Acid Derivative Formation: 2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be converted into boronic acids or esters through various transformations, including hydrolysis or treatment with appropriate reagents. These boronic acid derivatives are valuable intermediates in organic synthesis.
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2-(4-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolane
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4,4,5,5-Tetramethyl-2-(4-(trifluoromethyl)benzyl)-1,3,2-dioxaborolane
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4-((4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzonitrile
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Methyl 4-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)benzoate
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2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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2-(3-Chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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2-(3-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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(3-Methoxybenzyl)boronic Acid Pinacol Ester
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4,4,5,5-Tetramethyl-2-(3-(trifluoromethyl)benzyl)-1,3,2-dioxaborolane
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2-(4-Chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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