Chemistry
Organometallic Reagents
Organoboron
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline
Borylation Reactions: Due to the presence of the boronate ester group, this compound can undergo borylation reactions. For example, it can react with various boronating agents (e.g., boronic acids, boron trifluoride complexes) to form C-B bonds, converting the boronate ester group into a boronate.
Suzuki-Miyaura Cross-Coupling: The boronate ester group can participate in Suzuki-Miyaura cross-coupling reactions with aryl or vinyl halides (e.g., bromides, chlorides) in the presence of a palladium catalyst. This reaction can be used to introduce various aryl or vinyl substituents onto the indoline ring.
Amination Reactions: The nitrogen atom in the indoline ring can undergo amination reactions, such as Buchwald-Hartwig amination, to introduce various amine substituents onto the indoline ring.
Reductive Coupling: The boronate ester group can be converted into other functional groups through reductive coupling reactions. For example, it can be converted into an alcohol using reducing agents like sodium borohydride or lithium aluminum hydride.
Substitution Reactions: Depending on the reaction conditions, the substituents on the indoline ring can undergo various substitution reactions, such as nucleophilic aromatic substitution (SNAr) or electrophilic aromatic substitution (SEAr), to introduce different functional groups.
Oxidation Reactions: The boron atom in the boronate ester group can be oxidized to form a boronic acid or boronate ester, depending on the reaction conditions.
Cyclization Reactions: The molecule's structure may allow it to undergo cyclization reactions under specific conditions, leading to the formation of cyclic products.
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1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-1-yl)ethanone
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1-(Methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline
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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indoline
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1-(2-Methoxyethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline
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tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate