Borrowing Hydrogen Amination Reactions: A Complex Analysis of Trends and Correlations of the Various Reaction Parameters

ACS Catalysis, Год журнала: 2022, Номер 12(12), С. 7142 - 7198

Опубликована: Июнь 1, 2022

Borrowing hydrogen or the autotransfer amination is a powerful approach to create single C–N bonds, starting from stable and readily available substrates: amines alcohols. It considered as one of most atom-efficient green methods synthesize complex amines. Herein, we attempted arrange array existing data in comprehensive structured manner determine correlations between experimental conditions catalysis outcome both within different groups catalysts defined using machine analysis. For each type N-nucleophiles (aromatic, aliphatic, heteroaromatic amines, amides), efficient working were suggested, including attributing optimal base temperature regime for metal.

Язык: Английский

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Iridium supported on porous polypyridine-oxadiazole as high-activity and recyclable catalyst for the borrowing hydrogen reaction

Green Chemistry, Год журнала: 2022, Номер 24(6), С. 2602 - 2612

Опубликована: Янв. 1, 2022

Porous polypyridine-oxadiazole supported iridium catalysts (PPO-Ir) revealed high catalytic activity for the reaction of dimethyl-6-aminouracil (including 1,3-dimethylbarbituric acid, 2-aminobenzylamine) with alcohols.

Язык: Английский

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Recent Progress in the Synthesis of Heterocycles through Base Metal‐Catalyzed Acceptorless Dehydrogenative and Borrowing Hydrogen Approach

European Journal of Organic Chemistry, Год журнала: 2021, Номер 2021(26), С. 3690 - 3720

Опубликована: Июнь 15, 2021

Abstract Development in the area of acceptorless dehydrogenation (AD) and borrowing hydrogen (BH) catalysis emerge as one potential tools for various C−C C‐heteroatom bond forming reactions. Alcohols, which are important lignocellulosic biomass products, act pivotal electrophilic coupling partners such processes interestingly only H 2 or O is eliminated a byproduct. Initially, was developed by use noble metal catalysts. Recently, base metals Mn, Fe, Co, Ni proved to be environmentally benign inexpensive alternatives application AD BH methods. This transition catalyzed approaches also allow access toward plethora structurally heterocyclic molecules via atom economical strategy. Herein, we summarize current rising expansion heterocycles synthesis through hydrogenation

Язык: Английский

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Dehydrogenative Synthesis of Quinolines and Quinazolines via Ligand-Free Cobalt-Catalyzed Cyclization of 2-Aminoaryl Alcohols with Ketones or Nitriles

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 12596 - 12607

Опубликована: Сен. 26, 2022

We present a convenient and efficient protocol to synthesize quinolines quinazolines in one pot under mild conditions. A variety of substituted were synthesized good excellent yields (up 97% yield) from the dehydrogenative cyclizations 2-aminoaryl alcohols ketones catalyzed by readily available Co(OAc)2·4H2O. This cobalt catalytic system also showed high activity reactions 2-aminobenzyl with nitriles, affording various quinazoline derivatives 95% yield). The offers an environmentally benign approach for synthesis N-heterocycles employing earth-abundant salt ligand-free

Язык: Английский

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Well‐Defined Ni−SNS Complex Catalysed Borrowing Hydrogenative α‐Alkylation of Ketones and Dehydrogenative Synthesis of Quinolines

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(14), С. 2429 - 2437

Опубликована: Май 23, 2022

Abstract The “borrowing hydrogen” (BH) method for C‐alkylation reactions using alcohol as alkylating agents is an important synthetic transformation. In this respect, designing cheap and bench stable earth abundant metal catalyst borrowing hydrogen transformation a key challenge to be witnessed. Herein we have presented synthesis of non‐phosphine, easily accessible SNS−Ni complexes. Ni‐catalyst was successfully applied the ketone enolates α‐alkylated ketones. Primary with different functional groups various heteroaromatic alcohols are well tolerated. present system efficiently gram scale also green chemistry metrics reaction were calculated. protocol extended biologically quinoline moieties. Finally, control experiments deuterium labelled suggest that proceeds via pathway. magnified image

Язык: Английский

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Electronically tuneable orthometalated Ru^II–NHC complexes as efficient catalysts for C–C and C–N bond formations via borrowing hydrogen strategy

Catalysis Science & Technology, Год журнала: 2021, Номер 12(1), С. 67 - 74

Опубликована: Ноя. 10, 2021

A series of simple and electronically tuneable cyclometalated Ru II –NHC complexes have been explored as efficient catalysts for various C–C/N bond forming reactions via a BH methodology.

Язык: Английский

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Recent advances in C/N-alkylation with alcohols through hydride transfer strategies

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(39), С. 7713 - 7745

Опубликована: Янв. 1, 2022

Recent advances in C/N alkylation using alcohols as alkylating reagents via hydrogen-shuttle methodologies: Borrowing Hydrogen, Acceptorless Dehydrogenative Coupling, and Base-mediated Hydride Transfer.

Язык: Английский

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Copper-Mediated C4-Benzylations of 5-Aminopyrazoles with 3-Indoleacetic Acids

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 6623 - 6632

Опубликована: Май 11, 2023

Herein, we present a copper-mediated C4-benzylation of 5-aminopyrazoles with 3-indoleacetic acids. Various benzylated are prepared in good-to-excellent yields under basic and ligand-free conditions the presence copper acetate. Moreover, this benzylation method is applicable to other substrates, including naphthylamine, 2-aminochromen-4-one, enamines. Some products exhibit antiproliferative activities against cancer cell lines. In addition, C4-benzylated cyclized into 1H-pyrazolo[4',3':6,7]azepino[3,4-b]indoles aldehydes via one-pot two-step processes; notably, fluorescence emissions large Stokes shifts.

Язык: Английский

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Preparation of a novel cadmium-containing coordination polymer and catalytic application in the synthesis of N-alkylated aminoquinoline derivatives via the borrowing hydrogen approach

Dalton Transactions, Год журнала: 2024, Номер 53(11), С. 5064 - 5072

Опубликована: Янв. 1, 2024

Herein, we report an efficient and straightforward approach for the synthesis of

Язык: Английский

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3d Transition Metal Complexes as Homogeneous Catalysts in N-Alkylation Reactions Using Alcohols: A Recent Update

Tetrahedron, Год журнала: 2024, Номер 165, С. 134192 - 134192

Опубликована: Авг. 13, 2024

Язык: Английский

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