Metal-free synthesis strategies towards amide bond formation: review DOI Open Access

Fargana T. Alizadeh

PPOR, Год журнала: 2024, Номер 01, С. 163 - 163

Опубликована: Янв. 1, 2024

Amides are adaptable building blocks in synthetic organic chemistry that have a wide range of medicinal applications.They also employed as industrial raw materials for the wide-ranging production engineering plastics, detergents, and lubricants.A common reaction continues to be one most significant transformations is synthesis amides.Amide bond forming reactions critical both polypeptide chemistry.Most current approaches amidation employ stoichiometric activating agents, but such methods neither atom economical nor synthetically elegant.Catalytic potentially green more ideal substitutes standard thus subject this review.Building amide group crucial changes creation plan pharmaceutical sector.In order emphasize recent developments "dateless" reaction, with special focus on metal-free methodologies review provides an overview just relatively contributions been published previous few years.The present offers apt summary formation carboxylic acid substrates by taking advantage several methods.We show mechanisms representative detailed way numerous examples applications these bioactive compounds

Язык: Английский

Contemporary Approaches for Amide Bond Formation DOI
Paola Acosta‐Guzmán, Andrea Ojeda‐Porras, Diego Gamba‐Sánchez

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4359 - 4391

Опубликована: Ноя. 7, 2023

Abstract Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out thirty‐seven new drugs approved by FDA 2022, eleven are small molecules containing at least amide bond. Additionally, there nineteen large as drugs, some which have peptide structures, and therefore, also bear bonds. In years, multiple teams embraced challenge developing more efficient methods for formation. This dedication led numerous publications appearing monthly prestigious journals, showcasing advancements this field. The primary goal review is present viable strategies constructing It crucial differentiate between formation synthesis; hence, focus on describing specific forming C(O)−N particular, concentrates developed within last six years. There a particular emphasis approaches that consider thought process when selecting starting materials groups. approach ensures coverage all common chemical transformations yield

Язык: Английский

Процитировано

46

An Electrochemical Design for Catalytic Dehydration: Direct, Room-Temperature Esterification without Acid or Base Additives DOI
Jian Han,

Christopher A. Haines,

Jacob J. Piane

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(29), С. 15680 - 15687

Опубликована: Июль 12, 2023

An electrochemical approach has been leveraged to underpin a new conceptual platform for dehydration reactions, which demonstrated in the context of esterification. Esters were prepared from corresponding acid and alcohol partners at room temperature without or base additives consuming stoichiometric reagents. This methodology therefore addresses key complications that plague esterification reactions more broadly represent leading challenge synthetic chemistry.

Язык: Английский

Процитировано

18

On the Use of Triarylsilanols as Catalysts for Direct Amidation of Carboxylic Acids DOI Creative Commons
D. Christopher Braddock, Ben C. Rowley, Paul D. Lickiss

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 9853 - 9869

Опубликована: Июль 11, 2023

Triarylsilanols have been reported as the first silicon-centered molecular catalysts for direct amidation of carboxylic acids with amines identified after a screen silanols, silanediols, disiloxanediols, and incompletely condensed silsesquioxanes potential homogeneous catalysts. Subsequent synthesis testing various electronically differentiated triarylsilanols tris(p-haloaryl)silanols more active than parent triarylsilanol, where bromide congener is found to be most active. Catalyst decomposition can observed by NMR methods, but RPKA methods reveal that product inhibition operative, tertiary amides are inhibitory secondary amides. Studies using an authentically synthesized triaryl silylester putative intermediate in catalytic system enable plausible mechanism proposed supported computationals.

Язык: Английский

Процитировано

12

Synthesis of N-methyl secondary amides via diboronic acid anhydride-catalyzed dehydrative condensation of carboxylic acids with aqueous methylamine DOI

H. IWASAWA,

Naoya Takahashi, Naoyuki Shimada

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер 23(10), С. 2400 - 2410

Опубликована: Янв. 1, 2025

In this study, we present the first catalytic methodology for synthesizing N-methyl secondary amides via dehydrative condensation of hydroxycarboxylic acids with readily available and safe aqueous methylamine, employing diboronic acid anhydride (DBAA) as catalyst. DBAA catalysis can also be applied to direct amidations using ethylamine or dimethylamine. Moreover, demonstrate applicability system concise synthesis eight biologically active compounds containing β-amino alcohol motifs, including halostachine, synephrine, longimammine, phenylephrine, metanephrine, normacromerine, etilefrine, macromerine.

Язык: Английский

Процитировано

0

Direct Synthesis of Amides from Nitro Compounds and Alcohols via Borrowing Hydrogenation DOI

P. Madhavan Nair,

Gourishankar B. Swami,

Boopathy Gnanaprakasam

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 27, 2025

Herein, we report a RuH2(CO)(PPh3)3 catalyzed direct amidation of alcohols using readily available nitro compounds via catalytic borrowing hydrogen method. This reaction proceeded cascade reactions, including oxidation alcohol, reduction group and formation amides under one-pot condition. protocol provides single system for many step economic advantage over the techniques, tolerates various functionalities, was demonstrated with broad substrate scope (47 examples).

Язык: Английский

Процитировано

0

Recent update on the chemical modalities of mucoadhesive biopolymeric systems for safe and effective drug delivery DOI
Vivek Puri, Ameya Sharma, Divya Dheer

и другие.

Applied Materials Today, Год журнала: 2025, Номер 44, С. 102690 - 102690

Опубликована: Март 27, 2025

Язык: Английский

Процитировано

0

Synergistic optimization texture and functional behavior of 3D skeleton carbon using amide-functionalized and N-doped strategies for enhancement photocatalytic water reduction DOI
Jiahao Liu, Xuqiang Zhang,

Yi Guo

и другие.

International Journal of Hydrogen Energy, Год журнала: 2025, Номер 123, С. 32 - 40

Опубликована: Апрель 1, 2025

Язык: Английский

Процитировано

0

Photocatalytic Synthesis of Diaryl Amides via Direct Coupling of Methyl Arenes and Nitroarenes DOI

Robin Prakash Sirvin Rajan,

Chuanshi Hong, Kyung-Ho Park

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 17, 2025

A direct and effective method for synthesizing diaryl amides has been developed through the photocatalytic coupling of methyl nitroarenes. This employs FeCl3 as a redox-active photocatalyst under mild conditions to enable selective benzylic C-H activation concurrent nitro group reduction, eliminating necessity pre-functionalization. exhibits broad substrate scope, high functional tolerance, improved atom economy, offering sustainable practical alternative amide bond formation.

Язык: Английский

Процитировано

0

Fabrication of the Fe3O4/Cu-BTC Metal–Organic Framework Composite: A Magnetically Retrievable Efficient Catalytic Material for Hydration of Nitriles to Amides in Water DOI
Mayuri Dutta, Jyotismita Bora, G. C. Hazarika

и другие.

Chemistry of Materials, Год журнала: 2025, Номер unknown

Опубликована: Апрель 18, 2025

Язык: Английский

Процитировано

0

Nickel Catalyzed Carbonylation/Carboxylation Sequence via Double CO2 Incorporation DOI Creative Commons
Riccardo Giovanelli, Lorenzo Lombardi, Riccardo Pedrazzani

и другие.

Organic Letters, Год журнала: 2023, Номер 25(38), С. 6969 - 6974

Опубликована: Сен. 5, 2023

A carbonylation–carboxylation synthetic sequence, via double CO2 fixation, is described. The productive merger of a Ni-catalyzed cross-electrophile coupling manifold, with the use AlCl3, triggered cascade reaction formation three consecutive C–C bonds in single operation. This strategy traces an unprecedented route to ketones under Lewis acid assisted carbon dioxide valorization. Computational insights revealed unique function and labeling (13CO2) experiments validate genuine incorporation both functional groups.

Язык: Английский

Процитировано

10