Hydroarylation of unsaturated carbon–carbon bonds in cross-conjugated enynones under the action of superacid CF3SO3H or acidic zeolite HUSY. Reaction mechanism and DFT study on cationic intermediate species
Author:
Affiliation:
1. Department of Organic Chemistry
2. Institute of Chemistry
3. Saint Petersburg State University
4. Saint Petersburg
5. Russia
6. Department of Chemistry
7. Chemical Processes and Technologies
8. Togliatti State University
9. Togliatti
Abstract
Reactions of enynones with arenes in TfOH-Py or with zeolite HUSY lead to products of hydroarylation of the acetylene bond.
Funder
Russian Science Foundation
Publisher
Royal Society of Chemistry (RSC)
Subject
Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry
Link
http://pubs.rsc.org/en/content/articlepdf/2018/OB/C8OB01985A
Reference24 articles.
1. A Metal-Free Tandem C–C/C–O Bond Formation Approach to Diversely Functionalized Tetrasubstituted Furans
2. Ga(OTf)3-Promoted Sequential Reactions via Sulfur-Assisted Propargyl-Allenyl Isomerizations and Intramolecular [4 + 2] Cycloaddition for the Synthesis of 1,3-Dihydrobenzo[c]thiophenes
3. Transformations of Conjugated Enynones in the Superacid CF3SO3H. Synthesis of Butadienyl Triflates, Indanones, and Indenes
4. Facile access to 4-(1-alkynyl)-2(5H)-furanones by Sonogashira coupling of terminal acetylenes with β-tetronic acid bromide: efficient synthesis of cleviolide
5. Studies in biomimetic alkaloid syntheses. 14. Controlled, selective syntheses of catharanthine and tabersonine, and related desethyl compounds, through generation of 15-oxosecodine intermediates
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1. A General Synthesis of Cross-Conjugated Enynones through Pd Catalyzed Sonogashira Coupling with Triazine Esters;Molecules;2023-05-26
2. Cyclization of arylhydrazones of cross-conjugated enynones: synthesis of luminescent styryl-1H-pyrazoles and propenyl-1H-pyrazoles;Organic & Biomolecular Chemistry;2022
3. Triflic Acid Promoted Transformations of Linear‐Conjugated Enynones and their Reactions with Arenes. Synthesis of Dihydropyranones, Conjugated Dienones, and Indanes;European Journal of Organic Chemistry;2021-05-10
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