Scalable and Sustainable Reductive Amidation of Nitroarenes, Nitroalkenes, and Nitroalkyls with Acyl Saccharins in Aqueous Media DOI Creative Commons

Deákné Re,

Sunil L. Khamkar,

R. Mohan

и другие.

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Abstract We present a scalable and sustainable methodology for synthesizing N-substituted amides directly from readily available nitroarenes, nitroalkenes, nitroalkyls, acyl saccharin in aqueous media. This eco-friendly atom-efficient approach, which avoids column chromatography, demonstrates excellent functional group compatibility high yield key amide structures. The method's applicability extends to the formal synthesis of Disyprin, bromopyrrole alkaloid, as well amide-based pharmaceuticals agrochemicals. Additionally, we demonstrate its effectiveness multigram-scale paracetamol, alongside solvent recycling. A comprehensive Life Cycle Assessment (LCA; ISO 14044) was conducted evaluate environmental impacts sustainability nine selected Active Pharmaceutical Ingredients (APIs) produced via Non-Amidation Route (NAR) Amidation (AR). study reveals that saccharin-acetylation methods significantly reduce carbon footprints compared NAR is notably carbon-negative resource-efficient. Further impact reduction achievable through recycling adoption low-carbon renewable energy sources, highlighting potential saccharin-based processes substantially mitigate burdens pharmaceutical synthesis.

Язык: Английский

Recent advances of decatungstate photocatalyst in HAT process DOI
Praveen P. Singh, Surabhi Sinha, Prashant Gahtori

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(13), С. 2523 - 2538

Опубликована: Янв. 1, 2024

The decatungstate anion (W

Язык: Английский

Процитировано

29
Tetrabutylammonium decatungstate (TBADT), a compelling and trailblazing catalyst for visible-light-induced organic photocatalysis DOI
Bor‐Cherng Hong, Ranadheer Reddy Indurmuddam

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(19), С. 3799 - 3842

Опубликована: Янв. 1, 2024

Tetrabutylammonium decatungstate (TBADT) has recently emerged as an intriguing photocatalyst under visible-light or near-visible-light irradiation in a wide range of organic reactions that were previously not conceivable. Given its ability to absorb visible light and excellent effectiveness activating unactivated chemical bonds, it is promising addition traditional photocatalysts. This review covers some the contemporary developments photocatalysis enabled by TBADT catalyst 2023, with contents organized reaction type.

Язык: Английский

Процитировано

18
Recent progress in the synthesis of N-substituted arylamines by reductive cross-coupling of nitroarenes DOI

Jing‐Hao Qin,

Wang Yao,

Jun-Yao Ouyang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2638 - 2664

Опубликована: Янв. 1, 2024

This review describes the recent advances in different reaction types and catalytic systems for construction of C–NAr S–NAr bonds by nitroaromatic reductive cross-coupling.

Язык: Английский

Процитировано

12
Iron-Mediated Reductive Amidation of Triazine Esters with Nitroarenes DOI
Qing‐Dong Wang,

Xiang Liu,

Ya-Wen Zheng

и другие.

Organic Letters, Год журнала: 2023, Номер 26(1), С. 416 - 420

Опубликована: Дек. 31, 2023

A reductive amidation of triazine esters with nitroarenes by using cheap iron as a reducing metal in the presence TMSCl DMF was developed. The reactions proceeded efficiently under transition metal-free conditions to give corresponding amides moderate good yields functional group compatibility. Preliminary mechanistic investigations indicated that nitrosobenzene, N-phenyl hydroxylamine, azoxybenzene, azobenzene, aniline, and N-arylformamide possibly served intermediates reaction.

Язык: Английский

Процитировано

18
Palladium-Catalyzed Chelation-Assisted Aldehyde C–H Bond Activation of Quinoline-8-carbaldehydes: Synthesis of Amides from Aldehydes with Anilines and Other Amines DOI
Dinesh Gopichand Thakur,

Nileshkumar B. Rathod,

Sachinkumar D. Patel

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(2), С. 1058 - 1063

Опубликована: Янв. 9, 2024

A palladium-catalyzed chelation-assisted direct aldehyde C–H bond amidation of quinoline-8-carbaldehydes with an amine was developed under mild reaction conditions. wide range amides were obtained in good to excellent yields from a variety aniline derivatives and aliphatic amines. Our methodology successfully applied synthesize known DNA intercalating agents can be easily scaled up gram scale.

Язык: Английский

Процитировано

5
One-Pot Oxidative Amidation of Aldehydes via the Generation of Nitrile Imine Intermediates DOI Creative Commons
Martyn C. Henry,

Laura Minty,

Alexander C. W. Kwok

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7913 - 7926

Опубликована: Май 23, 2024

A one-pot procedure for the oxidative amidation of aldehydes via

Язык: Английский

Процитировано

4
Nickel-Catalyzed Amination of Aryl Halides: An Exogenous Ligand-Free Approach to Primary Arylamines Using Tmsn3 DOI
Jiawei Huang, Xiaoman Li, Zhigang Lei

и другие.

Опубликована: Янв. 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
Synthesis of amides via TBN-induced oxidation cross-coupling of acetonitrile and N -sulfinylanilines DOI

Quansen Wu,

Zhuang Ma, Rui Li

и другие.

Synthetic Communications, Год журнала: 2025, Номер unknown, С. 1 - 9

Опубликована: Апрель 21, 2025

Язык: Английский

Процитировано

0
A General Direct Aldehyde C–H Alkylation via TBADT-Nickel Synergistic Catalysis DOI
Zhimin Hu,

Ji‐Wei Sang,

Shuhua Xie

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 24, 2025

Herein, we present a nickel/tetrabutylammonium decatungstate (TBADT)-catalyzed protocol for general C-H alkylation of aldehydes, enabling the efficient synthesis aliphatic ketones through ligand-controlled cross-coupling. This mild and cost-effective methodology demonstrates broad substrate compatibility with various commercially available aldehydes both activated unactivated alkyl bromides, delivering target products in high yields. Notably, practical utility this catalytic system has been highlighted concise two-step valuable musk odorant Aurelione from readily starting materials.

Язык: Английский

Процитировано

0