Highly selective electrophilic B(9)-amination of o-carborane driven by HOTf and HFIP

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(18), С. 4975 - 4980

Опубликована: Янв. 1, 2022

An efficient B(9) electrophilic amination of o -carboranes with azodicarboxylates, promoted by a Brønsted acid and HFIP, was developed.

Язык: Английский

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A strategy for regioselective B–H functionalization ofo-carboranesviabase metal catalysis

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(12), С. 3074 - 3079

Опубликована: Янв. 1, 2023

This frontier article summarizes the recent developments in base metal-catalyzed regioselective cage B–H functionalization of carboranes and discusses related challenging issues.

Язык: Английский

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N‐Ligand‐Enabled Aromatic Nucleophilic Amination of 1,2‐Diaryl‐o‐Carboranes with (R₂N)₂Mg for Selective Synthesis of 4‐R₂N‐o‐Carboranes and 2‐R₂N‐m‐Carboranes

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(32)

Опубликована: Май 17, 2022

The nucleophilic aromatic BH substitution reaction of carboranes is uncommon, compared to the electrophilic one. This work reported a pyridine-enabled transition-metal-free regioselective cage B(4)-H amination 1,2-diaryl-o-carboranes with magnesium bisamides, giving series B(4)-aminated o-carboranes. DFT calculations showcased stepwise B-N formation/B-H cleavage process, in which Mg-H formation/cage closure rate-determining step. Unprecedentedly, presence 4,4'-di-tert-butyl-2,2'-dipyridyl (dtbpy), tandem B(4)-amination/cage isomerization o-carboranes was discovered for facile preparation B(2)-aminated m-carboranes. Control experiments indicated that complex, bidentate ligand (dtbpy) and temperature were crucial process. direct B-H offers an alternative strategy selective o-

Язык: Английский

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Iridium-catalyzed selective arylation of B(6)–H of 3-aryl-o-carboranes with arylboronic acid via direct B–H activation

Chemical Communications, Год журнала: 2024, Номер 60(9), С. 1124 - 1127

Опубликована: Янв. 1, 2024

This work discloses an iridium-catalyzed selective arylation of B(6)–H 3-Ar- o -carboranes with arylboronic acid via direct B–H activation for the first time.

Язык: Английский

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Palladium-Catalyzed Selective B(3)-Esterification of o-Carboranes with CO and Alcohols

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 3, 2025

Selective functionalization of o-carboranes has received tremendous attention, specifically in the regioselective modification ten chemically similar BH vertices within o-carborane cage. We disclose herein a strategy for palladium-catalyzed esterification B(3)-H bond using tungsten hexacarbonyl as carbon monoxide source. The corresponding functionalized were prepared moderate to very good yields with excellent regioselectivity.

Язык: Английский

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Self-reducing Cu2O/Cu nanosheet interface for efficient electrocatalytic production of ammonium from nitrate

Applied Catalysis B Environment and Energy, Год журнала: 2025, Номер unknown, С. 125254 - 125254

Опубликована: Март 1, 2025

Язык: Английский

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Palladium-Catalyzed Regioselective B(3,4)–H Acyloxylation of o-Carboranes

Inorganic Chemistry, Год журнала: 2021, Номер 61(2), С. 911 - 922

Опубликована: Дек. 29, 2021

We disclose herein an efficient regioselective B(3,4)-H activation via a ligand strategy, affording B(3)-monoacyloxylated and B(3,4)-diacyloxylated o-carboranes. The identification of amino acid phosphoric ligands is crucial for the success B(3)-mono- B(3,4)-diacyloxylation, respectively. This approach compatible with broad range carboxylic acids. functionalization complex drug molecules demonstrated. Other acyloxyl sources, including sodium benzoate, benzoic anhydride, iodobenzene diacetate, are also tolerated.

Язык: Английский

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Iridium-Catalyzed Selective B(4)–H Amination of o-Carboranes with Anthranils

Organic Letters, Год журнала: 2022, Номер 24(39), С. 7077 - 7081

Опубликована: Сен. 23, 2022

We report here a catalytic selective cage B4-H amination of o-carboranes employing an Ir(III) complex as catalyst and anthranils aminating agents, leading to large class B4-aminated with very high yields broad substrate scope under mild conditions without any oxidants. In these reactions, the carboxyl group serves traceless directing unit determine site selectivity degree substitution.

Язык: Английский

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How substituents at boron atoms affect the CH-acidity and the electron-withdrawing effect of the ortho-carborane cage: A close look on the 1H NMR spectra

Inorganica Chimica Acta, Год журнала: 2022, Номер 547, С. 121339 - 121339

Опубликована: Дек. 9, 2022

Язык: Английский

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Rhodium-catalyzed sequential B(3)-, B(4)-, and B(5)-trifunctionalization of o-carboranes with three different substituents

Chemical Communications, Год журнала: 2021, Номер 58(5), С. 629 - 632

Опубликована: Дек. 8, 2021

A rhodium-catalyzed one-pot trifunctionalization of o-carboranes with three different substituents via a carboxy group directed sequential B(5)-alkenylation, B(4)-alkyne annulation and B(3)-acyloxylation has been developed for the first time, leading to synthesis new class B(3,4,5)-trisubstituted o-carborane derivatives. Treatment 1-COOH-2-CH3-o-C2B10H10 ArCCAr in presence [Cp*RhCl2]2 catalyst Cu(OPiv)2 oxidant gave 1,4-[COOC(Ar)C(Ar)]-2-Me-3-OPiv-5-[C(Ar)CH(Ar)-o-C2B10H7 good high yields. This protocol represents strategy catalytic selective polyfunctionalization carboranes substituents.

Язык: Английский

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