Mild and Stereoselective Synthesis of (1E,3E)-Dienes through Silver(I)-Catalyzed β-Hydride Migration from Allylic α-Diazo Esters DOI
Marcus M. Sá, Pedro A. M. Moro,

Theo V. C. Russo

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3741 - 3751

Published: July 18, 2024

Abstract A mild procedure for the diastereoselective preparation of functionalized 1,3-dienes and their synthetic versatility are described herein. The silver-catalyzed decomposition α-diazo-γ,δ-unsaturated esters through β-hydride migration at room temperature resulted in stereoselective formation 12 conjugated (1E,3E)-dienes. Further post-modifications included intramolecular Heck reaction hydrogenation, leading to a novel substituted indene an aliphatic diester, respectively. To rationalize observed outcome, computational investigation mechanisms was conducted, emphasizing importance factors such as metallocarbenoid stability, substituent effects, microkinetics simulations better understand intricacies.

Language: Английский

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation DOI Creative Commons
Sourav Behera, Shyamal Kanti Bera, Francesco Basoccu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2035 - 2043

Published: Feb. 8, 2024

Abstract Our research has demonstrated that mechanochemical activation is more effective with solid reagents. We have showcased the practicality of Bertagnini's salts, also called aldehyde‐bisulfite adducts, which are crystalline, simplifying preparation and storage. These salts stable substitutes for liquid aldehydes ketones been employed in reductive amination, synthesizing aza‐heterocycles hydrazones within mechanochemistry. The technique‘s effectiveness broadens substrate scopes, simplifies purification, reduces reaction times, yields desired products ranging from 38–91%. Additionally, thermal stability bisulfite adducts confirmed through TGA (Thermogravimetric analysis) analysis.

Language: Английский

Citations

3
Rhodium-Catalyzed Formal Four-Component Reaction with Hypervalent Iodine Diazoesters, Alcohols, and Isatins for the Synthesis of Multi-functionalized Oxindoles DOI
Jie Tang, Xiaoyan Yang,

Gejun Niu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(4), P. 1106 - 1111

Published: Dec. 18, 2023

A novel Rh( ii )-catalyzed formal four-component reaction involving hypervalent iodine diazoesters, alcohols, and isatins was effectively established as an efficient process to produce multi-functionalized oxindoles in good high yields.

Language: Английский

Citations

4
Transition-Metal- and Photocatalyst-Free Photoinduced Formation of Carbon–Pnictogen (–N, –P) Bonds DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(17), P. 2627 - 2637

Published: April 2, 2024

Abstract Pnictogens, classified within group 15 elements, play a pivotal role in the constitution of diverse array drug molecules, natural products, and functional materials. Recent research has increasingly prioritized exploration mild conditions for synthesizing C–Pnictogen (C–N C–P) bonds, highlighting growing emphasis on efficient sustainable synthetic methodologies. This Short Review explores fundamental mechanisms, addresses constraints, assesses methodologies, underscoring potential photocatalyst- transition-metal-free photochemical reactions advancing sustainability. Divided into two segments, it encompasses recent advancements facilitating C–N C–P bond formation. 1 Introduction 2 Carbon–Nitrogen (C–N) Bond Formation 3 Carbon–Phosphorus (C–P) 4 Summary Outlook

Language: Английский

Citations

1
Pioneering Metal‐Free Late‐Stage C‐H Functionalization Using Acridinium Salt Photocatalysis DOI Creative Commons
Shyamal Kanti Bera, Andrea Porcheddu

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(67)

Published: Aug. 13, 2024

Abstract Using organic dyes as photocatalysts is an innovative approach to photocatalytic transformations. These offer advantages such widespread availability, adaptable absorption properties, and diverse chemical structures. Recent progress has led the development of that can utilize visible light modify chemically inert C−H bonds. catalysts are sustainable, selective, versatile, enabling mild reactions, late‐stage functionalization, various transformations in line with green chemistry principles. As photoredox chemistry, they contribute efficient environmentally friendly synthetic pathways. Acridinium‐based have proved valuable transformative reactions under conditions. This review emphasizes their features, frameworks, applications modifying complex molecules. It provides overview recent advancements use acridinium‐based for bond functionalization without need transition metals, showcasing potential expedite new molecules igniting excitement about prospects this research field.

Language: Английский

Citations

1
Synthesis of 3-Substituted Chromones through Photoactivation of Acceptor–Acceptor Diazo Compounds DOI
Namrata Rastogi, Prashant Kumar, Asit Kumar

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 4, 2024

Abstract We report the photocatalytic alkylation of o-hydroxyarylenaminones with acceptor–acceptor diazo compounds to access 3-alkyl chromones. The reaction involves triplet sensitization substrate via energy transfer from photosensitizer. notable features protocol are operational simplicity, wide scope, and generally high yields products.

Language: Английский

Citations

0
Mild and Stereoselective Synthesis of (1E,3E)-Dienes through Silver(I)-Catalyzed β-Hydride Migration from Allylic α-Diazo Esters DOI
Marcus M. Sá, Pedro A. M. Moro,

Theo V. C. Russo

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3741 - 3751

Published: July 18, 2024

Abstract A mild procedure for the diastereoselective preparation of functionalized 1,3-dienes and their synthetic versatility are described herein. The silver-catalyzed decomposition α-diazo-γ,δ-unsaturated esters through β-hydride migration at room temperature resulted in stereoselective formation 12 conjugated (1E,3E)-dienes. Further post-modifications included intramolecular Heck reaction hydrogenation, leading to a novel substituted indene an aliphatic diester, respectively. To rationalize observed outcome, computational investigation mechanisms was conducted, emphasizing importance factors such as metallocarbenoid stability, substituent effects, microkinetics simulations better understand intricacies.

Language: Английский

Citations

0