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Palladium-Catalyzed Dual C-H Arylation/Cyclization Reaction of Iodoferrocenes with -Bromobenzamides for the Construction of Arylated Isoquinolone-Fused Ferrocenes.
J Org Chem
December 2024
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China.
We reported a palladium/norbornene-catalyzed dual intermolecular C-H arylation/intramolecular cyclization reaction of iodoferrocenes with -bromobenzamides, enabling the formation of arylated isoquinolone-fused ferrocenes in a straightforward and effective manner. This method has a broad substrate scope and good functional group compatibility, while the gram-scale reaction demonstrates the practicality of this method.
View Article and Find Full Text PDFPalladium-catalyzed annulation and intermolecular hydroamination involving norbornene derivatives: synthesis of indanones and -alkylamines.
Chem Commun (Camb)
December 2024
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang 473061, China.
A palladium-catalyzed divergent reaction of primary benzamides using norbornene (NBE) derivatives as a controlled switch is reported. When NBE is used as a mediator, indanones are synthesized with moderate to good yields a Catellani reaction that involves sequential -C-H alkylation and -C-N bond cleavage annulation of primary benzamides. Employing norbornadiene (NBD) instead of NBE enables the assembly of -alkylamines by an intermolecular hydroamination reaction.
View Article and Find Full Text PDFPalladium-Catalyzed Cyclization and Direct Arylation of 1-[2-(2,2-Dibromoethenyl)phenyl]-1-pyrrole with Allenes.
J Org Chem
October 2024
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
Article Synopsis
- A new palladium-catalyzed reaction was developed to efficiently create pyrrolo[1,2-]quinolones from a specific compound involving allenes.
- The process combines two key steps: cyclization and direct arylation, resulting in the formation of multiple new chemical bonds and rings.
- This method is versatile and can work with various substrates and functional groups effectively.
Hydroxylamines: From Synthetic Intermediates to Synthetic Targets.
Acc Chem Res
October 2024
School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore.
ConspectusSynergy between the teaching and research activities of a University should be a source of new ideas, each informing the other. A classroom discussion gave rise to our concept of using hydroxylamines as a form of "tethered nitrogen" for alkaloid synthesis. The "tether" temporarily connects a nucleophilic nitrogen atom to the substrate, rendering an intermolecular reaction intramolecular, thus providing stereo- and regiochemical control for C-N bond formation.
View Article and Find Full Text PDFPalladium-Catalyzed Synthesis of β-Alkynyl Ketones via Selective 1,3-Alkynyl Migration of α,α-Disubstituted Allylic Alcohols.
J Org Chem
September 2024
College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.
Herein, a palladium-catalyzed 1,3-alkynyl migration of allylic alcohol for the synthesis of β-alkynyl ketone was described. This intramolecular rearrangement reaction demonstrated an enhanced reactivity compared to the traditional intermolecular alkynylation by circumventing the dimerization of alkynes, exhibiting a specific selectivity toward β-alkynyl elimination. Moreover, this reaction featured wide substrate scope, good functional group tolerance, and 100% atom economy.
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