Two novel types of elegant three-component reactions of stable isochromenylium tetrafluoroborates (ICTBs) have been developed under mild metal-free conditions in this work. Mechanistically, these reactions are commonly initiated by a [4+2]-cycloaddition between the non-classical isochromenylium diene and the aldehyde-enol, and terminated by the following addition of weak nucleophiles, including nitriles or the second equivalent of aldehydes, in a one-pot fashion. The developed methodologies exhibit excellent chemoselectivity, regioselectivity, and diastereoselectivity, and provide a new convenient access to functionalized dihydronaphthalenes and tetrahydronaphthalenes.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201002317 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Ruthenium-catalyzed three-component tandem remote C-H functionalization of naphthalenes: modular and concise synthesis of multifunctional naphthalenes.
Chem Sci
December 2024
Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Hubei University Wuhan 430062 P. R. China
The prevalence of naphthalene compounds in biologically active natural products, organic ligands and approved drugs has motivated investigators to develop efficient strategies for their selective synthesis. C-H functionalization of naphthalene has been frequently deployed, but mainly involves two-component reactions, while multiple-component C-H functionalization for the synthesis of naphthalene compounds has thus far proven elusive. Herein, we disclose a versatile three-component protocol for the modular synthesis of multifunctional naphthalenes from readily available simple naphthalenes, olefins and alkyl bromides P(iii)-assisted ruthenium-catalyzed remote C-H functionalization.
View Article and Find Full Text PDFA one-pot, acid-, base-, and metal-free, multicomponent strategy has been developed to synthesize spiro thiochromene-oxindole derivatives as potential anti-inflammatory agents. The synthesized compounds were screened for their anti-inflammatory activity by inhibiting heat-induced Bovine Serum Albumin (BSA) denaturation assay, revealing moderate to good efficacy. Compounds 4e, 4k, and 4h exhibited the highest activity, inhibiting BSA denaturation by 90.
View Article and Find Full Text PDFElectrochemical Three-Component C-H Functionalization of Indoles with Sodium Bisulfite and Alcohols to Access Indole-Containing Sulfonate Esters.
J Org Chem
January 2025
Jiangxi Provincial Key Laboratory of Organic Functional Molecules, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China.
Herein, an efficient electrochemical three-component C-H functionalization of indoles with sodium bisulfite and alcohols is described, providing a sustainable and convenient synthetic route for the construction of structurally valuable indole-containing sulfonate esters in moderate to good yields. This protocol proceeds in an undivided cell without any metal catalysts or oxidants, features a broad substrate scope, and has an excellent functional group tolerance. Preliminary mechanistic studies suggest that a radical-radical pathway may be involved in this three-component reaction system.
View Article and Find Full Text PDFSolvent-Controlled Cascade Reaction of SeO, Sulfonyl Hydrazides and Alkynes for Chemoselective Access to Symmetric Divinyl Sulfones Substituted Seleniums and Diseleniums.
Org Lett
January 2025
College of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, People's Republic of China.
A solvent-controlled unprecedented tandem reaction of readily accessible SeO, a wide variety of sulfonyl hydrazides, and alkynes has been established for the chemodivergent construction of structurally complex 1,2-bis(()-1-aryl-2-arylsulfonylvinyl)diselanes and bis(()-1-aryl-2-(arylsulfonyl)vinyl)selanes via a catalyst-free one-pot three-component approach, respectively. The adjustable and controlled synthetic strategy shows good yields and chemoselectivities for most substrates under mild and simple conditions.
View Article and Find Full Text PDFSuzuki-Miyaura/Mizoroki-Heck coupling cascade to access 2,2'-bifunctionalized biaryls.
Chem Commun (Camb)
January 2025
Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh 226031, India.
Biaryl motifs are essential structural features in several drugs and functional molecules. Cyclic diaryliodonium has been scarcely explored as a bifunctional agent compared to ring opening and annulation reactions. Herein, a three-component cascade approach is developed to synthesize bifunctionalized biaryls employing cyclic diaryliodoniums as a biarylating agent.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!