Synthesis of Carboxylic Acids Containing α-All-Carbon Quaternary Centers from Diazo Compounds and Trialkylboranes DOI
Yuan‐Ze Xu, Yan Xu, Jianbo Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

The construction of C–C bonds to form all-carbon quaternary centers remains a significant challenge in synthetic chemistry. Herein, we report tandem process involving 1,2-migration tetra-coordinated boron intermediate followed by Claisen rearrangement the enolate, achieved through reaction between allyl diazoacetates and trialkylboranes. transformation forms two at carbenic position diazo substrate single-step operation under neutral conditions. Using this method, successfully realized gram-scale formal total synthesis Vincamine, an indole alkaloid with pharmacological activity.

Language: Английский

Tosylhydrazide-Induced 1,6-Enyne Radical Cyclization under Copper Catalysis: Access to 3,4-Dihydronaphthalen-1(2H)-one Derivatives DOI

Yeganeh Sadat Hosseini Nasab,

Saideh Rajai‐Daryasarei,

Frank Röminger

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 30, 2024

We describe an approach to access 4-aroyl-3-aryl-3,4-dihydronaphthalen-1(2H)-one derivatives in 41–79% yields through the Cu-catalyzed radical cyclization/desulfonylation of 1,6-enynes with tosylhydrazide under air conditions. This alternative desulfonylation strategy combines mild conditions, external oxidant-free processes, and sustainability, contributing more environmentally friendly organic synthesis. The mechanistic studies showed that CuCl/O2 combination serves as source oxygen atom needed form C═O bond. existence is crucial for this conversion.

Language: Английский

Citations

1
Asymmetric dearomatization of benzyl 1-naphthyl ethers via [1,3] O-to-C rearrangement DOI

Hongkun Zeng,

Gang Wen, Lili Lin

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(58), P. 7507 - 7510

Published: Jan. 1, 2024

An asymmetric dearomatization reaction of benzyl 1-naphthyl ethers accelerated by a chiral N , ′-dioxide/Co( ii ) complex is disclosed. Experiment results indicated that the proceeds via tight ion-pair intermediate.

Language: Английский

Citations

1
Electrogenerated Lewis Acid-Catalyzed Claisen Rearrangement of Allyl Aryl Ethers DOI

Yuta Niki,

Koichi Mitsudo, Eisuke F. Sato

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 16, 2024

Catalysts for Claisen rearrangement have been intensively studied to overcome the need high temperature. However, previous studies encountered challenges, such as heating, a long reaction time, and/or equivalent amounts of catalyst. In this study, we introduce an effective electrogenerated boron-based Lewis acid catalyst aromatic rearrangement, which proceeds in few minutes at ambient Generation is discussed based on NMR analysis and DFT calculations.

Language: Английский

Citations

1
Rearrangement reactions: Important tool for the synthesis of piperazines DOI
Upasna Sharma, Rajnish Kumar, Avijit Mazumder

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(13), P. 1031 - 1050

Published: May 22, 2024

A six-membered heterocyclic compound known as piperazine has two nitrogen atoms within a ring. Numerous studies have shown that the potential to be useful pharmacophore in many harmful pharmacological conditions, such microbiocidal, anti-inflammatory, anticancer, antioxidant, etc. In this present review, we highlighted synthetic protocols for and its analogs protocol via rearrangement reactions been adopted recent years. The study also involved listing of several patents (granted), which comprised important work on derivatives. Among all methods, most commonly methods included synthesis by diaza-cope, hydrolytic, Mumm, Ugi-smiles, [2 + 3] Stevens, Aza-witting, Curtius, Schmidt reactions, These compared based different reaction feasibility, economy help researchers designing their work.

Language: Английский

Citations

0
Atom-Efficient Chlorinative Dearomatization of Naphthol, Quinolinol, and Isoquinolinol Derivatives using Trichloroisocyanuric Acid (TCCA) DOI

Jenna D. Caudle,

Mary Ennis,

Dillon C. Dodge

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 30, 2024

A variety of dearomatized compounds have been prepared in moderate to excellent yields from planar scaffolds using trichloroisocyanuric acid (TCCA) as an atom-economical chlorinating agent. The method tolerates a broad range functionalities and can take place several green and/or sustainable solvents. Twenty-one examples 1,1-dichlorinated products 2-naphthols analogous heteroarenes (quinolinols, isoquinolinols, quinazolinol) are reported along with five monochlorinated products. utility the 1,1-dichloronaphthalenone product reactive intermediate species is demonstrated two-step, one-pot reaction carried out solvent. In mechanistic investigation, coordination agent hydroxy substituent scaffold prior chlorine transfer implicated.

Language: Английский

Citations

0
Synthesis of Carboxylic Acids Containing α-All-Carbon Quaternary Centers from Diazo Compounds and Trialkylboranes DOI
Yuan‐Ze Xu, Yan Xu, Jianbo Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

The construction of C–C bonds to form all-carbon quaternary centers remains a significant challenge in synthetic chemistry. Herein, we report tandem process involving 1,2-migration tetra-coordinated boron intermediate followed by Claisen rearrangement the enolate, achieved through reaction between allyl diazoacetates and trialkylboranes. transformation forms two at carbenic position diazo substrate single-step operation under neutral conditions. Using this method, successfully realized gram-scale formal total synthesis Vincamine, an indole alkaloid with pharmacological activity.

Language: Английский

Citations

0