Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c3cc40577j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Tetracyclic-Fused Dihydroindeno[2,1-]chromenes via Palladium-Catalyzed Alkyne Insertion and C-H Bond Activation.
J Org Chem
December 2024
Jiangsu Key Laboratory for Chemistry of Low Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, China.
An unprecedented Pd-catalyzed cascade alkyne insertion/Heck/C-H activation reaction of -iodophenyl alkenyl ethers and diarylacetylenes has been developed. Diversified tetracyclic-fused dihydroindeno[2,1-]chromenes bearing a quaternary center were constructed in an efficient, straightforward, and atom-economic way with good to excellent yields. The protocol features high bonding efficiency, operational simplicity, broad substrate scope, and easy scale-up.
View Article and Find Full Text PDFPalladium-Catalyzed Carbonylative Sonogashira Coupling of Aliphatic Alkynes and Aryl Thianthrenium Salts to Alkynones and Furanones.
Org Lett
December 2024
Leibniz-Institut für Katalyse e.V., Albert-Einstein-Straße 29a, 18059 Rostock, Germany.
Herein, we developed a mild and efficient palladium-catalyzed carbonylative Sonogashira coupling of aryl thianthrenium salts with aliphatic alkynes and benzyl acetylene toward alkynones and furanones. Various desired products were prepared in good yields with broad functional group tolerance including the bromide group. In the case of using benzyl acetylene, the corresponding furanones can be obtained in good yields under the same conditions with two molecules of CO inserted.
View Article and Find Full Text PDFDFT Studies on the Mechanism of Ligand-Regulated Palladium-Catalyzed Iodide-Assisted Hydrocarbonylation of Olefins with Formic Acid: Favored Reaction Routes and Selectivities.
J Org Chem
December 2024
Department of Basic Education, Shanxi Agricultural University, Jinzhong, Shanxi 030801, P. R. China.
DFT calculations have been performed to gain insight into the mechanism of hydrocarbonylation of olefins and the origin of regio- and chemoselectivity. It is shown that the most feasible mechanism involves five steps: (i) decomposition of acetic formic anhydride, (ii) hydropalladation of olefins, (iii) CO migratory insertion, (iv) iodide-assisted acetate-formate exchange, and (v) formylation or carboxylation. Importantly, carboxylation proceeds via the decomposition of anhydride, followed by reductive elimination instead of direct hydrolysis of anhydride.
View Article and Find Full Text PDFSite-selective decarbonylative [4 + 2] annulation of carboxylic acids with terminal alkynes by C-C/C-H activation strategy and cluster catalysis.
Chem Sci
December 2024
School of Chemistry and Chemical Engineering, Hainan University Haikou 570228 China
Article Synopsis
- The manuscript presents a novel palladium-catalyzed cyclization method using carboxylic acids and terminal alkynes, which showcases its potential for creating complex organic molecules.
- This technique is significant as it allows carboxylic acids, traditionally underutilized, to serve as effective building blocks in intramolecular cycloaddition and addresses long-standing challenges in synthesizing substituted naphthalenes.
- The reaction demonstrates a wide range of substrate compatibility and functional group tolerance, making it applicable for scalable synthesis in organic chemistry, drug discovery, and material science.
Ring-Enlargement of in Situ Generated Cyclopropanones by the Reaction with Sulfonium Ylides: One-Pot Synthesis of Cyclobutanones.
Org Lett
November 2024
Institute of Organic Chemistry, Albert-Ludwigs-Universität Freiburg, 79104 Freiburg im Breisgau, Germany.
In this report, we describe a simple method for the synthesis of 2-aryl-2-vinyl-cyclobutanones through the reaction of in situ generated cyclopropanones and cinnamylsulfonium ylides, representing an example of a formal carbene insertion into these three-membered rings. The cyclobutanones thus obtained are ideal substrates for palladium-catalyzed coupling reactions upon enol triflate formation, thereby providing access to densely functionalized cyclobutenes. A mechanistic proposal for the ring-enlargement is presented based on experimental evidence.
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!