Borrowing Hydrogen for Organic Synthesis

ACS Central Science, Journal Year: 2021, Volume and Issue: 7(4), P. 570 - 585

Published: March 25, 2021

Borrowing hydrogen is a process that used to diversify the synthetic utility of commodity alcohols. A catalyst first oxidizes an alcohol by removing form reactive carbonyl compound. This intermediate can undergo diverse range subsequent transformations before returns "borrowed" liberate product and regenerate catalyst. In this way, alcohols may be as alkylating agents whereby sole byproduct one-pot reaction water. recent decades, significant advances have been made in area, demonstrating many effective methods access valuable products. outlook highlights diversity metal biocatalysts are available for approach, well various performed, focusing on selection most advances. By succinctly describing conveying versatility borrowing chemistry, we anticipate its uptake will increase across wider scientific audience, expanding opportunities further development.

Language: Английский

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

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(12), P. 7142 - 7198

Published: June 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.

Language: Английский

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Chromium‐Catalyzed Alkylation of Amines by Alcohols

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(29), P. 11789 - 11793

Published: March 18, 2020

Abstract The alkylation of amines by alcohols is a broadly applicable, sustainable, and selective method for the synthesis alkyl amines, which are important bulk fine chemicals, pharmaceuticals, agrochemicals. We show that Cr complexes can catalyze this C−N bond formation reaction. synthesized isolated 35 examples alkylated including 13 previously undisclosed products, use amino as alkylating agents was demonstrated. catalyst tolerates numerous functional groups, hydrogenation‐sensitive examples. Compared to many other alcohol‐based amine methods, where stoichiometric amount base required, our Cr‐based system gives yields higher than 90 % various with catalytic base. Our study indicates borrowing hydrogen or autotransfer reactions could thus be an alternative Fe, Co, Mn, noble metals in (de)hydrogenation catalysis.

Language: Английский

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A Fe single atom on N,S-doped carbon catalyst for performing N-alkylation of aromatic amines under solvent-free conditions

Journal of Materials Chemistry A, Journal Year: 2021, Volume and Issue: 9(44), P. 25128 - 25135

Published: Jan. 1, 2021

A green and gram-scale strategy has been developed for the synthesis of Fe single atom/N,S-doped carbon catalyst via pyrolysis polyaniline-modified Fe,S-doped ZIFs, in which ZIFs can be prepared water at room temperature.

Language: Английский

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

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(6), P. 2602 - 2612

Published: Jan. 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.

Language: Английский

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Atomic-Level Asymmetric Tuning of the Co₁–N₃P₁ Catalyst for Highly Efficient N-Alkylation of Amines with Alcohols

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(29), P. 20518 - 20529

Published: July 12, 2024

Despite the extensive development of non-noble metals for

Language: Английский

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Reusable Co-nanoparticles for general and selective N-alkylation of amines and ammonia with alcohols

Chemical Science, Journal Year: 2021, Volume and Issue: 13(1), P. 111 - 117

Published: Nov. 29, 2021

A general cobalt-catalyzed

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Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(16), P. 10377 - 10382

Published: Aug. 5, 2021

An example of homogeneous Mo-catalyzed direct N-alkylation anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective challenging alcohols. enhanced strategy should be useful in designing highly active systems for borrowing hydrogen transformations.

Language: Английский

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Ruthenium(ii) complexes with N-heterocyclic carbene–phosphine ligands for the N-alkylation of amines with alcohols

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(15), P. 3451 - 3461

Published: Jan. 1, 2021

A Ru catalyst with the hetero-bidentate NHC-phosphine ligand, which realizes N-alkylation of amines alcohols improved catalytic activity.

Language: Английский

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Guerbet-type β-alkylation of secondary alcohols catalyzed by chromium chloride and its corresponding NNN pincer complex

Catalysis Science & Technology, Journal Year: 2022, Volume and Issue: 12(15), P. 4753 - 4762

Published: Jan. 1, 2022

β-Alkylation of alcohols has been efficiently accomplished using readily available 3d metal Cr under microwave conditions in air. Well-defined molecular is involved with a KIE 7.33 and insertion α-alkylated ketone into Cr–H bond as the RDS.

Language: Английский

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