The transition-metal free fluoroalkylation of vinyl azides is herein reported. This operationally simple reaction employs the Togni reagent as a CF3 source, Bu4 NI as an initiator, and occurs under electron catalysis. A range of readily prepared starting materials are functionalized using this approach to produce both phenanthridines and quinoxalin-2-ones.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201602855 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Copper-Mediated -CF(OCF)(CFH) Transfer to Organic Electrophiles.
ACS Org Inorg Au
December 2024
Department of Chemistry and Biomolecular Sciences and Centre for Catalysis Research and Innovation, University of Ottawa, 30 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
The integration of fluorine into medicinal compounds has become a widely used strategy to improve the biochemical and therapeutic properties of drugs. Inclusion of -CFH and -OCF fluoroalkyl groups has garnered attention due to their bioisosteric properties, enhanced lipophilicity, and potential hydrogen-bonding capability in bioactive substances. In this study, we prepared a series of stable Cu[CF(OCF)(CFH)]L complexes by insertion of commercially available perfluoro(methyl vinyl ether), CF=CF(OCF), into Cu-H bonds derived from Stryker's reagent, [CuH(PPh)], using ancillary ligands L.
View Article and Find Full Text PDFLight-Driven Organocatalyzed Controlled Radical Copolymerization of (Perfluoroalkyl)ethylenes and Vinyl Esters/Amides.
ACS Macro Lett
December 2024
Department of Macromolecular Science, State Key Laboratory of Molecular Engineering of Polymers, Fudan Univesity, Shanghai 200433, China.
Article Synopsis
- Fluoropolymers have great potential for high-tech applications, but synthesizing them from simple monomers is challenging.
- This research introduces a new method using organocatalyzed controlled radical copolymerization to create fluoropolymers without metals, allowing for customizable side-chain fluorinated polymers through light irradiation.
- The resulting fluoropolymers have desirable properties like good chain-end fidelity, low dispersity, adjustable compositions, and excellent light transmission capabilities.
Stereoselective Fe-Catalyzed Decoupled Cross-Couplings: Chiral Vinyl Oxazolidinones as Effective Radical Lynchpins for Diastereoselective C(sp)-C(sp) Bond Formation.
ACS Catal
September 2024
Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
Modular, catalytic, and stereoselective methods for the dicarbofunctionalization of alkenes can streamline the synthesis of chiral active pharmaceutical ingredients (APIs) and agrochemicals. However, despite the inherent attractive properties of iron as catalysts for practical pharmaceutical synthesis (i.e.
View Article and Find Full Text PDFFe-Catalyzed Fluoroalkyl(hetero)arylation of Vinyl Azaarenes: Rapid and Modular Synthesis of Unsymmetrical 1,1-Bis(hetero)arylalkanes.
Org Lett
August 2024
Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States.
In contrast to transition-metal-catalyzed difunctionalization of activated alkenes, selective alkylarylation of vinyl azaarenes is underdeveloped. Consequently, the lack of modular and rapid syntheses of 1,1-bis(hetero)arylalkanes limits their exploration in medicinal chemistry. Herein we report a protocol using commercially available iron salts, bisphosphine ligands, fluoroalkyl halides, and Grignard reagents that enables the selective 1,2-fluoroalkyl(hetero)arylation of vinyl azaarenes.
View Article and Find Full Text PDFCombining (CHO) and (NH)CO as a Formamidine Equivalent for "Four-in-One" Synthesis of Fluoroalkylated 2--Pyrimidines.
Org Lett
August 2024
Technical Institute of Fluorochemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
Multicomponent reactions hold the potential to maximize the synthetic efficiency in the preparation of diverse and complex molecular scaffolds. An unprecedented formal [3+1+1+1] annulation approach for the one-step synthesis of fluoroalkylated 2--pyrimidines commencing from perfluoroalkyl alkenes, paraformaldehyde, and ammonium carbonate is described. By harnessing readily accessible (CHO) and cheap (NH)CO as a formamidine surrogate, this method effectively replaces traditionally preformed amidines with a pyrimidine assembly.
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!