ChemInform Abstract: Borrowing Hydrogen. C—N Bond Formation from Alcohols

Lamb, Gareth W.; Williams, Jonathan M. J.

doi:10.1002/chin.200935228

Cited by 3 publications

(5 citation statements)

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“…In particular contribution of Milstein and co-workers in development of direct homogeneous catalytic amination of primary alcohols with ammonia should be acknowledged [104]. Transformations of secondary alcohols to primary amines with ammonia following the so-called hydrogen borrowing methodology were described extensively in the literature [7,64,105,[110][111][112][113][114][115][116][117][118][119][120][121][122].…”

Section: Homogeneous Catalystsmentioning

confidence: 99%

Valorization of Biomass Derived Terpene Compounds by Catalytic Amination

2018

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This review fills an apparent gap existing in the literature by providing an overview of the readily available terpenes and existing catalytic protocols for preparation of terpene-derived amines. To address the role of solid catalysts in amination of terpenes the same reactions with homogeneous counterparts are also discussed. Such catalysts can be considered as a benchmark, which solid catalysts should match. Although catalytic systems based on transition metal complexes have been developed for synthesis of amines to a larger extent, there is an apparent need to reduce the production costs. Subsequently, homogenous systems based on cheaper metals operating by nucleophilic substitution (e.g., Ni, Co, Cu, Fe) with a possibility of easy recycling, as well as metal nanoparticles (e.g., Pd, Au) supported on amphoteric oxides should be developed. These catalysts will allow synthesis of amine derivatives of terpenes which have a broad range of applications as specialty chemicals (e.g., pesticides, surfactants, etc.) and pharmaceuticals. The review will be useful in selection and design of appropriate solid materials with tailored properties as efficient catalysts for amination of terpenes.

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Section: Homogeneous Catalystsmentioning

confidence: 99%

Valorization of Biomass Derived Terpene Compounds by Catalytic Amination

2018

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“…Since lignocellulose can be processed to alcohols, , the development of reactions converting alcohols to the diversity of bulk and fine chemicals containing carbon is a central topic in sustainable or green chemistry . The alkylation of amines by alcohols is an early and chemically important example of an alcohol refunctionalization reaction. − It can proceed as shown in Scheme . , The alcohol starting material is oxidized via dehydrogenation. The two hydrogen atoms, which were removed from the alcohol, are parked at the catalyst.…”

Section: Introductionmentioning

confidence: 99%

“…The complexes shown in Scheme were used as catalysts or precatalysts. If ammonia is used as the nucleophile, as first demonstrated by the groups of Baiker (heterogeneous), Milstein, and Fujita and Yamaguchi (homogeneous), the OH group of the alcohol starting material is converted directly into a NH 2 group or a primary aliphatic amine. − Similarly, C-alkylation reactions can proceed − with the central C–C coupling step being an aldol type of condensation (Scheme ). The first example was the Guerbet reaction. , In recent years, a variety of elegant catalytic syntheses permitting alkyl–alkyl C–C coupling reactions have been developed. − More recently, the selective dimerization of ethanol has been disclosed. , Nearly all these early developments have been mediated by rare noble metal catalysts, based on Ru or Ir mostly.…”

Section: Introductionmentioning

confidence: 99%

“…In addition, Quintard and co-workers summarized “Recent Achievements in Enantioselective Borrowing Hydrogen by the Combination of Iron- and Organocatalysis” . A review with the focus of our work has not been published to the best of our knowledge. − The catalyst systems discussed here are ordered by catalytically active metal and in chronological order. We always describe the N-alkylation first followed by C-alkylation catalysis.…”

Section: Introductionmentioning

confidence: 99%

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3d-Metal Catalyzed N- and C-Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer

2018

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The conservation of our element resources is a fundamental challenge of mankind. The development of alcohol refunctionalization reactions is a possible fossil carbon conservation strategy since alcohols can be obtained from indigestible and abundantly available biomass. The conservation of our rare noble metals, frequently used in key technologies such as catalysis, might be feasible by replacing them with highly abundant metals. The alkylation of amines by alcohols and related C–C coupling reactions are early examples of alcohol refunctionalization reactions. These reactions follow mostly the borrowing hydrogen or hydrogen autotransfer catalysis concept, and many 3d-metal catalysts have been disclosed in recent years. In this review, we summarize the progress made in developing Cu, Ni, Co, Fe, and Mn catalysts for C–N and C–C bond formation reactions with alcohols and amines using the borrowing hydrogen or hydrogen autotransfer concept. We expect that the findings in this field will inspire others to develop new efficient and selective earth-abundant metal catalysts for borrowing hydrogen or hydrogen autotransfer applications or to develop novel alcohol refunctionalization reactions that can be mediated by such metals.

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“…12,13 In modern chemistry, alcohol has emerged as a crucial electrophile for the synthesis of coupling compounds via the hydrogen auto-transfer approach and the ADC (acceptorless dehydrogenation coupling) strategies. 14 In 2021, Maiti and co-workers reported recent progress in the transition metal-catalyzed oxidative olefination of sp 2 and sp 3 C–H bonds. 15 This review article focuses on the acceptorless dehydrogenation coupling strategy among various olefination methodologies.…”

Section: Introductionmentioning

confidence: 99%