A Cooperative Rh/Co‐Catalyzed Hydroaminomethylation Reaction for the Synthesis of Terpene Amines

Alonso, Alejandro Pérez; Minh, Doan Pham; Plá, Daniel; Gómez, Montserrat

doi:10.1002/cctc.202300501

Cited by 4 publications

(2 citation statements)

References 40 publications

(44 reference statements)

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“…The reaction conditions (feedstock composition) were calculated to obtain a theoretical H 2 /CO ratio of ca. 1.8, which is a suitable ratio for downstream hydroaminomethylation 42 and Fischer−Tropsch processes. 43 The performance of the catalysts was evaluated with regard to the CH 4 and CO 2 conversions.…”

Section: Characterization Of the Prepared Ni-based Catalytic Materialsmentioning

confidence: 99%

Advanced Nickel-Based Catalytic Materials on Hydroxyapatite: Effect of the Metal Particle Size on Tri-reforming of Methane

Alonso,

Serrano-Maldonado,

Ledeuil

et al. 2024

ACS Sustainable Resour. Manage.

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A new strategy based on an organometallic approach for the preparation of Ni-based catalytic materials permitting control of the morphology and distribution of the nanoparticles on the support has been developed, leading to spherical, small (mean diameter below 5 nm), and homogeneously distributed nickel nanoparticles on hydroxyapatite. The as-prepared materials were characterized by different techniques (N 2 physisorption, powder X-ray diffraction, transmission electron microscopy, infrared spectroscopy, temperature-programmed reduction, temperature-programmed desorption of ammonia, temperature-programmed desorption of carbon dioxide, and thermogravimetric analyses, among the most relevant). The catalytic performance of these materials was evaluated in the tri-reforming of methane at 800−850 °C and 1.4 bar (molar feed composition CH 4 :CO 2 :H 2 O:O 2 = 63.3:30.7:0.04:5.95, gas hourly space velocity = 14.9 L•g cat −1•h −1 ), in view of syngas production. Outstanding catalytic performance, in terms of activity, selectivity, and stability, were achieved with the catalysts prepared via an organometallic method precluding structural modifications on the support. A comparative study between these catalytic materials proved higher activity and stability of the aforementioned materials in comparison with those prepared by a conventional incipient wetness impregnation methodology, mainly associated with stronger metal support interactions and higher surface area.

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Section: Characterization Of the Prepared Ni-based Catalytic Materialsmentioning

confidence: 99%

Advanced Nickel-Based Catalytic Materials on Hydroxyapatite: Effect of the Metal Particle Size on Tri-reforming of Methane

Alonso,

Serrano-Maldonado,

Ledeuil

et al. 2024

ACS Sustainable Resour. Manage.

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“…Many of these reduction steps require the presence of a catalyst to activate the reducing agent [4], and transition-metals (such as Ru, Rh, Pd, Ag, Ir, Pt, and Au) have also been used extensively [5] in the preparation of active pharmaceutical ingredients (APIs) [6,7]. Despite its cost, Rh shows remarkable activity for such a reaction, as shown in the recent literature [8][9][10][11], and has the potential to be employed in robust hydrogenation catalysts with low metal loading. A Rh/Al 2 O 3 -catalyzed reductive amination of furfural and other aldehydes, especially those associated with biomass, was recently reported by Chatterjee, Kawanami, and coworkers using an aqueous solution of NH 3 [12].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Reductive Amination under Heterogeneous Catalysis for the Synthesis of β-Adrenergic Agonist and Related Structures

Bucciol,

Colia,

Canova

et al. 2023

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Reductive amination is a powerful tool in sustainable organic synthesis that allows chemists to access a wide range of valuable amine products using renewable feedstocks and mild reaction conditions, with minimal waste generation. Practical applications can be found in various fields, including pharmaceuticals, contributing to greener and more sustainable chemical processes. In this work, we present a heterogeneous (Rh and Pt) catalyzed protocol for the fast and efficient synthesis of ractopamine hydrochloride (β-adrenergic drug) under microwave-assisted reductive amination protocol starting from raspberry ketone and octopamine. Microwave (MW) successfully accelerated the hydrogenation reaction and reduced the reaction time from 13 h to only 3 h under mild conditions (50 °C at 10 bar). The best catalysts were Pt/C and Rh/C, which led to high conversion and selectivity towards ractopamine:HCl. Different solvents and ketone substrates were also experimented. Acetophenone, cyclohexanone, and 2-butanone reacted at lower H2 pressure (5 bar), and highest selectivity was observed with cyclohexanone (99%). These preliminary experiments may be useful for further process improvements in the synthesis of β-adrenergic agonists and related structures and underline the positive synergy between MW and heterogeneous catalysis.

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Antiproliferative in Vitro Evaluation of Terpenic Amines Synthesized via a Rhodium‐catalyzed Hydroaminomethylation

Pérez Alonso,

Gibot,

Favier

et al. 2024

Chemistry & Biodiversity

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Terpene‐derived alkaloids show a variety of biological activities, including antioxidant, anti‐inflammatory, antimicrobial and cytotoxicity effects. In this work, homologated monoterpene amines have been prepared via a rhodium‐catalyzed hydroaminomethylation of biomass‐based alkenes, such as (R)‐limonene, linalool, myrcene and camphene, in combination with secondary amines of aliphatic and aromatic nature, namely morpholine and N‐methylaniline, leading to highly chemo‐ and regioselective processes. The as‐prepared amines were obtained in 50‐99% overall yields, and in vitro tested on a human colon cancer cell line (HCT‐116) to evaluate their cytotoxic potential. The lead compound of the series (3a) showed cytotoxicity in the micromolar range (IC50 52.46 µM) via the induction of cell death by apoptosis, paving the way towards further structure‐activity relationship studies.

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A Cooperative Rh/Co‐Catalyzed Hydroaminomethylation Reaction for the Synthesis of Terpene Amines

Cited by 4 publications

References 40 publications

Advanced Nickel-Based Catalytic Materials on Hydroxyapatite: Effect of the Metal Particle Size on Tri-reforming of Methane

Advanced Nickel-Based Catalytic Materials on Hydroxyapatite: Effect of the Metal Particle Size on Tri-reforming of Methane

Microwave-Assisted Reductive Amination under Heterogeneous Catalysis for the Synthesis of β-Adrenergic Agonist and Related Structures

Antiproliferative in Vitro Evaluation of Terpenic Amines Synthesized via a Rhodium‐catalyzed Hydroaminomethylation

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