Mechanochemical Deprotection of t-Butoxycarbonyl (Boc) Group Using Basic Alumina DOI

Kaidi Tian,

Tingna Cai,

Zedong Zhu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(38), P. 7811 - 7816

Published: Jan. 1, 2024

A solvent-free, operationally simple, and chemoselective mechanochemical method for

Language: Английский

Visible Light-Driven Flexible Synthesis of α-Alkylated Glycine Derivatives Catalyzed by Reusable Covalent Organic Frameworks DOI

Yao Tian,

Xiubin Bu,

Luohe Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1657 - 1668

Published: Jan. 19, 2024

Herein, we report a heterogeneous visible light-driven preparation of α-alkylated glycine derivatives. This approach employed β-ketoenamine-linked covalent organic framework (2D-COF-4) as the photocatalyst and N-hydroxy phthalimide (NHPI) esters alkyl radical sources. Numerous derivatives, including dipeptides, were precisely efficiently alkylated under reaction conditions. Based on excellent photoactivity compatibility 2D-COF-4, this alkylation could proceed flexibly in green solvent (ethanol) without any other additives. The fruitfully recycled with simple workup procedure, revealing high ecoscale value low environmental factor (E-factor).

Language: Английский

Citations

4

Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control DOI
Keyu Xiang, Haowen Shou, Chenhui Hu

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(10), P. 5890 - 5899

Published: Jan. 1, 2024

A novel approach utilizing the polymer-assisted grinding (POLAG) technique to facilitate regioselective oxidative Heck coupling of aryl boronic acids with electronically unbiased olefins under solvent-free conditions was presented.

Language: Английский

Citations

4

Ethanol-assisted mechanochemical asymmetric cross-dehydrogenative coupling reaction with recoverable chiral amine/NaCl for accessing chiral α-alkyl α-glycine derivatives DOI
Jingbo Yu, Hongsong Chen,

Ziwen Zhang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6570 - 6577

Published: Jan. 1, 2024

Ethanol-assisted grinding effectively facilitated aerobic asymmetric cross-dehydrogenative coupling of glycine esters/amides with ketones/aldehydes, deploying reusable chiral amine/NaCl for rapid synthesis α-alkyl α-glycine derivatives.

Language: Английский

Citations

3

Mechanochemical C−H Arylation and Alkylation of Indoles Using 3 d Transition Metal and Zero‐Valent Magnesium DOI
Chongyang Wu,

LV Jin,

Hangqian Fan

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(26)

Published: Jan. 31, 2024

Although the 3 d transition-metal catalyzed C-H functionalization have been extensively employed to promote formation of valuable carbon-carbon bonds, persistent problems, including use sensitive Grignard reagents and rigorous operations (solvent-drying, inert gas protection, metal pre-activation RMgX addition rate control), still leave great room for further development sustainable methodologies. Herein, we report a mechanochemical technology toward in-situ preparation highly organomagnesium reagents, thus building two general catalytic platforms that enables regioselective arylation alkylation indoles with wide variety halides (including those containing post transformable functionalities heteroaromatic rings). This strategy also brings unique reactivity high step-economy in producing functionalized N-free indole products.

Language: Английский

Citations

2

Green and rapid acid-catalyzed ynamide skeletal rearrangement and stereospecific functionalization with anisole derivatives DOI
Mohana Reddy Mutra,

T. L. Chandana,

Yun-Jou Wang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 8124 - 8133

Published: Jan. 1, 2023

Environmentally friendly acid-catalyzed 2-alkynyl-ynamides (N–Csp) bond cleavage, alkyne migration and stereospecific functionalization with anisole derivatives for the synthesis of challenging indole scaffolds in 5–10 minutes.

Language: Английский

Citations

6

Iron-catalyzed asymmetric Csp3–H/Csp3–H coupling: improving the chirality induction by mechanochemical liquid-assisted grinding DOI

Ping Ying,

Ying Tao, Hong Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 127 - 134

Published: Nov. 10, 2023

A mechanochemical iron-catalyzed asymmetric oxidative coupling between glycines and β-ketoesters has been disclosed, utilizing t -BuOH to improve the enantioselectivity stabilize iminium intermediate via intensified hydrogen bond interactions.

Language: Английский

Citations

4

Total Mechano-synthesis of 2-Cyclopropyl-4-(4-Fluorophenyl) Quinoline-3-Acrylaldehyde—A Pivotal intermediate of Pitavastatin DOI Creative Commons
Jingbo Yu, Yanhua Zhang, Zehao Zheng

et al.

RSC Mechanochemistry, Journal Year: 2024, Volume and Issue: 1(4), P. 367 - 374

Published: Jan. 1, 2024

A new three-step mechano-synthesis method starts with 4-bromoquinoline, uses Suzuki–Miyaura, Minisci C–H alkylation, and oxidation Heck coupling reactions, leading to rapid eco-friendly synthesis of the key Pitavastatin intermediate.

Language: Английский

Citations

1

Mechanochemical Radical Transformations in Organic Synthesis DOI

Jon Sperry,

Sahra Sheikhaleslami

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 22, 2024

Abstract Organic synthesis has historically relied on solution‐phase, polar transformations to forge new bonds. However, this paradigm is evolving, propelled by the rapid evolution of radical chemistry. Additionally, organic witnessing a simultaneous resurgence in mechanochemistry, formation bonds solid‐state, further contributing shift status quo. The aforementioned advances chemistry have predominantly occurred solution phase, while majority mechanochemical feature transformations. Herein, we discuss rapidly advancing area synthesis: reactions. Solid‐state reactions offer improved green metrics, better reaction outcomes, and access intermediates products that are difficult or impossible reach solution. This review explores these context small molecule synthesis, from early findings current state‐of‐the‐art, underscoring pivotal role solid‐state likely play sustainable chemical synthesis.

Language: Английский

Citations

1

Electrochemical Construction of C–S Bond: A Green Approach for Preparing Sulfur-Containing Scaffolds DOI Creative Commons

Ruonan Zou,

Jingbo Yu,

Ping Ying

et al.

Pharmaceutical Fronts, Journal Year: 2024, Volume and Issue: 06(01), P. e9 - e19

Published: March 1, 2024

Abstract The organosulfur frameworks containing C–S bonds are important structural motifs in various biologically active molecules and functional materials. In this regard, transition-metal catalysis using chemical oxidants to prime reactions has emerged as the most common method, however, is prone several side such dimerization overoxidation. recent years, organic electrosynthesis become a hot topic due its eco-friendly mild process which costly catalysts toxic could be replaced by electrons. This perspective summarized recently developed bond protocols, discussing highlighting reaction features, substrate scope, well application pharmaceuticals, underlying mechanisms. study helps development of electrochemical process-enabled construction future.

Language: Английский

Citations

0

Mechanochemical Deprotection of t-Butoxycarbonyl (Boc) Group Using Basic Alumina DOI

Kaidi Tian,

Tingna Cai,

Zedong Zhu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(38), P. 7811 - 7816

Published: Jan. 1, 2024

A solvent-free, operationally simple, and chemoselective mechanochemical method for

Language: Английский

Citations

0