Chemistry Organometallic Reagents Organoborons 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-1H-Indole

5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-1H-Indole

Suzuki-Miyaura Cross-Coupling Reaction: This reaction involves coupling the boron-containing compound with an aryl or vinyl halide or triflate in the presence of a palladium catalyst, typically a Pd(PPh3)4 complex. The reaction forms a new carbon-carbon bond between the boron atom and the halide or triflate, resulting in the incorporation of the indole moiety into more complex molecules. Boronic Acid Pinacol Ester Formation: The compound can be converted into its boronic acid pinacol ester derivative, which is a valuable intermediate in various synthetic transformations. This can be achieved by treating it with pinacolborane (HBPin) in the presence of a Lewis acid or base. Hydrolysis: The boron-oxygen bond in the boron-containing compound can be hydrolyzed under acidic or basic conditions, leading to the cleavage of the boron atom from the indole ring. Functionalization Reactions: Various functional groups can be introduced onto the indole ring using standard synthetic methods. For example, halogenation, alkylation, acylation, and other substitution reactions can be performed on the indole ring. Reduction Reactions: The compound can undergo reduction reactions, such as the reduction of the boron atom to its corresponding boronic acid or alcohol derivative using reducing agents like sodium borohydride (NaBH4). Formation of Complexes: The boron atom in the compound can form complexes with various Lewis bases or Lewis acids, leading to the generation of structurally interesting and potentially reactive species.

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(1-(Tert-Butoxycarbonyl)-1H-Indol-2-Yl)Boronic Acid (1-Phenyl-1H-Pyrazol-4-Yl)Boronic Acid (1H-Indazol-4-Yl)Boronic Acid (1H-Indazol-6-Yl)Boronic Acid (1H-Indol-2-Yl)Boronic Acid (2,3-Dichlorophenyl)Boronic Acid (2,3-Difluorophenyl)Boronic Acid (2,6-Dichlorophenyl)Boronic Acid (2,6-Difluorophenyl)Boronic Acid (2-(Phenoxymethyl)Phenyl)Boronic Acid (2-(Trifluoromethoxy)Phenyl)Boronic Acid (2-(Trifluoromethyl)Phenyl)Boronic Acid (2-Bromophenyl)Boronic Acid (2-Chloro-3-Methoxyphenyl)Boronic Acid (2-Chloro-6-Fluorophenyl)Boronic Acid (2-Fluoro-3-(Trifluoromethyl)Phenyl)Boronic Acid (2-Fluorophenyl)Boronic Acid (2-Nitrophenyl)Boronic Acid (3,4-Dichlorophenyl)Boronic Acid (3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenyl)Methanol (3-(Benzyloxy)Phenyl)Boronic Acid (3-(Phenoxymethyl)Phenyl)Boronic Acid (3-(Phenylcarbamoyl)Phenyl)Boronic Acid (3-(Trifluoromethoxy)Phenyl)Boronic Acid (3-(Trifluoromethyl)Phenyl)Boronic Acid (3-Bromo-2-Fluorophenyl)Boronic Acid (3-Bromo-2-Methoxyphenyl)Boronic Acid (3-Bromophenyl)Boronic Acid (3-Chloro-2-Methoxyphenyl)Boronic Acid (3-Chloro-4-Fluorophenyl)Boronic Acid (3-Chlorophenyl)Boronic Acid (3-Fluorophenyl)Boronic Acid (3-Iodophenyl)Boronic Acid (3-Nitrophenyl)Boronic Acid (4-(Benzyloxy)Phenyl)Boronic Acid (4-(Methylsulfonyl)Phenyl)Boronic Acid (4-(Phenoxymethyl)Phenyl)Boronic Acid (4-(Phenylcarbamoyl)Phenyl)Boronic Acid (4-(Trifluoromethyl)Phenyl)Boronic Acid (4-Cyclohexylphenyl)Boronic Acid (4-Fluorophenyl)Boronic Acid (5-(Trifluoromethyl)Pyridin-3-Yl)Boronic Acid (6-Phenoxypyridin-3-Yl)Boronic Acid (9H-Fluoren-2-Yl)Boronic Acid (E)-4,4,5,5-Tetramethyl-2-Styryl-1,3,2-Dioxaborolane 1,3,2-Dioxaborinane 1-(4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzyl)Piperazine 1-(4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenyl)Piperazine 1-(5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridin-2-Yl)Piperazine 1-Methyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-1H-Pyrazole 2,7-Bis(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-9H-Fluorene 2-(1,3,2-Dioxaborinan-2-Yl)Benzonitrile 2-(1,3,2-Dioxaborolan-2-Yl)-1-Methyl-1H-Indole 2-(2-(Bromomethyl)Phenyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(2-Bromophenyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(3-Chlorophenyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(3-Cyclopropylphenyl)-1,3,2-Dioxaborolane 2-(3-Isopropoxyphenyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzonitrile 2-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenol 2-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-(4-(Benzyloxy)Phenyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(4-Bromophenyl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(4-Cyclopropylphenyl)-1,3,2-Dioxaborolane 2-(4-Fluorophenyl)-1,3,2-Dioxaborinane 2-([1,1'-Biphenyl]-4-Yl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(Cyclohex-1-En-1-Yl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(Furan-2-Yl)-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-(M-Tolyl)-1,3,2-Dioxaborinane 2-Benzyl-4,4,5,5-Tetramethyl-1,3,2-Dioxaborolane 2-Chloro-3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-Chloro-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-Chloro-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-Fluoro-3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-Methoxy-3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-Methoxy-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-Methyl-3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 2-Methyl-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 3-(1,3,2-Dioxaborinan-2-Yl)Aniline 3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzonitrile 3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 3-Chloro-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 3-Fluoro-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 3-Methyl-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 4,4,5,5-Tetramethyl-2-(2-(Trifluoromethyl)Phenyl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(2-Nitrophenyl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(3-(Trifluoromethoxy)Phenyl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(Naphthalen-1-Yl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(Naphthalen-2-Yl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(Thiophen-2-Yl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(Thiophen-3-Yl)-1,3,2-Dioxaborolane 4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-1,2,3,6-Tetrahydropyridine 4-Methyl-3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridine 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-1H-Indole 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Indoline 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Nicotinonitrile 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyridin-2-Amine 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Pyrimidine 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Thiazole [1,1'-Biphenyl]-4-Ylboronic Acid Benzo[B]Thiophen-2-Ylboronic Acid Benzofuran-2-Ylboronic Acid Benzyl (4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Phenyl)Carbamate Cyclohex-1-En-1-Ylboronic Acid Ethyl 3-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzoate Isoquinolin-4-Ylboronic Acid Methyl 5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Nicotinate N,N-Diphenyl-4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Aniline Naphthalen-1-Ylboronic Acid Naphthalen-2-Ylboronic Acid Phenylboronic Acid Pyridin-2-Ylboronic Acid Pyridin-3-Ylboronic Acid Pyridin-4-Ylboronic Acid Pyrimidin-5-Ylboronic Acid Tert-Butyl 2-(1,3,2-Dioxaborolan-2-Yl)-1H-Indole-1-Carboxylate Tert-Butyl 4-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)-1H-Pyrazole-1-Carboxylate Tetraphenylborate Thiophen-2-Ylboronic Acid

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Alkenyl-Phenyl-Boronic-Acid Amino-Methyl-Phenyl-Borate Amino-Phenyl-Boronic-Acid Benzofuran-Boronic Acid Boronate-Piperidine-Carboxylate Bromophenyl-Boronate Bromopyridine-Boronate Butoxy-Phenyl-Boronic-Acid Carbazolyl-Phenyl-Boronic-Acid Carbonyl-Phenyl-Boronic-Acid Chloro-Phenyl-Boronic-Acid Chlorpyridine-Boronate Dimethyldioxaborane Dioxaborolan-Carbazole Dioxaborolan-Indazole Dioxaborolan-Indole Dioxaborolan-Methanol Dioxaborolan-Pyrazole Dioxaborolan-Pyrimidine Dioxaborolane Dioxaborolane-Benzene Dioxaborolane-Benzimidazole Dioxaborolane-Benzoxazole Dioxaborolane-Indene Dioxaborolane-Morpholine Dioxaborolane-Piperazine Dioxaborolane-Piperidine Dioxaborolane-Pyrrole Dioxaborolane-Pyrrolidine Dioxaborolane-Quinoline Dioxaborolane-Thiazole Fluorene-Boric Acid Fluorene-Boric-Acid Fluorene-Boronic Acid Fluorene-Dioxaborolane Fluorene-Phenyl-Boronic Acid Fluorene-Phenyl-Boronic Acid/Ester Fluorene-Phenyl-Boronic-Acid Fluoro-Phenyl-Boronic Acid Fluoro-Pyridine-Borate Fluorophenyl-Borate Formamidophenylboronic-Acid Hydroxymethyl-Phenyl-Boronic-Acid Hydroxyphenyl-Boronate Indazol-Boronic Acid Isopropoxyphenylboronic Isopropyl-Phenyl-Boronic-Acid Isoquinolin-Boronic-Acid Methoxy-Pyridine-Boronate Methoxyphenylboronic Acid Methoxyphenylboronic-Acid Methylthio-Phenyl-Boronic-Acid Naphthenic-Benzene-Boronic-Acid Phenyl-Boronate Phenyl-Boronic-Acid-Carboxylate Phenyl-Naphthalene-Boronic Acid Phenyl-Naphthalene-Boronic Acid/Ester Phenyl-Naphthalene-Boronic-Acid Phenylboronic Picoline-Boronate Piperidinyl-Phenyl-Boronic-Acid Potassium Methyltrifluoroborate Potassium Trifluoroborate Pyrazole-Phenyl-Boronic-Acid Pyridine-Boronate Pyridineamine-Borate Pyridineboronic Acid Pyridone Boronate Pyridyl-Benzene-Boronic-Acid Pyridyl-Phenyl-Borate Pyrrolidine-Benzene-Boronic-Acid Quinoline-Dioxaborolane Sulfonyl-Phenyl-Boronic Acid Thienyl-Benzene-Boronic-Acid Thiophene-Boronic Acid Trifluoromethyl-Phenyl-Borate Trifluoromethyl-Phenyl-Boronic Acid Trifluorotoluene-Dioxaborane

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    6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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    6-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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    Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate

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    Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate

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    5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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    5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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    3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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    3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

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    Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carboxylate

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    Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carboxylate

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